Vacation Home Rentals By Owner In Siesta Key, FL

$875.93

Combined Beachfront Bliss - Aloha Kai #24 & #24N - Roelens

Siesta Key, Florida, United States

Aloha Kai #24 & #24N (Combined Villas)brBeachfrontbrbrA Siesta Key Beachside Bliss Awaits!brbrStep into the tropical luxury of Aloha Kai #24 & #24N, where the gentle waves of Crescent Beach and the laid-back spirit of Siesta Key create a dream escape. This combined beachfront haven blends the charm of two villas into one perfect getaway, offering a seamless mix of relaxation and adventure. Aloha Kai #24 & #24N invites you to unwind with the sound of the Gulf, sip coffee on your private patios, and dive into a sun-soaked paradise—book your island retreat today! Here's what makes this home so special:brbrBedding Arrangement: brbrAloha Kai #24:br2 Bedrooms:brMaster Suite: King-size bed, Smart TVbrGuest Bedroom 1: Two Twin-size beds, Smart TVbrSleep Sofa in the Living RoombrAloha Kai #24N:br1 Bedroom:brMaster Suite: King-size bed, Smart TVbrTop Features:brSleeps 8brLargest Pools on Siesta Key: Plunge into the expansive, sparkling pools surrounded by spacious lounging decks with ample lounges, tables, and chairs for ultimate sun-soaked relaxation. brDirect Beach Access Points: Just steps from the powdery white sands of Crescent Beach, rated #1 in the U.S., with shaded pavilions and lounge chairs for your comfort.brRelaxing Back Porch with Beach View and Grill: Unwind on cozy porch with morning coffee or savor romantic evenings with a grill and beach views.brCommunity Amenity Sets: Enjoy shuffleboard, ping pong, and poolside community rooms, plus complimentary beach toys and floats for endless seaside fun.brPerfect Home Base Location: Stroll to nearby restaurants, ice cream spots, and bars, or hop on the Siesta Key trolley for island exploration, with activities for all ages and nature lovers.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #24 & #24N places you at the heart of Crescent Beach, renowned for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded pavilion, strolling the 3-mile shoreline, or watching stunning Gulf sunsets, this dual-villa gem offers tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be effortless and memorable. Book your Siesta Key escape at Aloha Kai #24 & #24N today!brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future!brbrDISCLAIMERS:br10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.brThis home does not allow pets.brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property. Every Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

3

Bed

2

Bath

8

Sleeps

$214.43

/ Nightly

Private Vacation Home

Stay at Coastal Charm: Siesta Key Monthly Rental with Pool on Canal

Siesta Key, Florida, United States

Coastal Charm by Tropical Sands Accommodations brbrWelcome to Coastal Charm, a refreshed 3-bedroom, 2-bath Siesta Key home located just a 10-minute walk to Siesta Key Beach and close to the shops and restaurants of Siesta Key Village. This peaceful canal front property features a private pool, outdoor dining, and dog friendly options. Perfect for families and small groups seeking a long-term stay on Florida’s most beloved barrier island. With a 30-night minimum stay, it’s ideal for extended vacations and seasonal living. brbrHighlights br• 10-minute walk to Siesta Key Beach br• 3 Bedrooms / 2 Bathrooms br• 2 Kings, Twin over Twin Bunks br• Canal front house br• Private heated Pool and Lounge Chairs br• Outdoor Dining and BBQ Grill br• Beach Chairs and Beach Cart br• Washer and Dryer br• Dog Friendly (with approval and fee) br• 3 Parking Spaces brbrCoastal Charm’s backyard is designed for relaxation, offering a sparkling private pool, plenty of lounge chairs, and a canal front backdrop. The covered outdoor dining area includes a BBQ grill, making it easy to enjoy breezy meals throughout your stay. Beach chairs and a beach cart are provided for convenient days at the shoreline, while the peaceful neighborhood setting enhances your long term comfort. brbrInside, the home features a warm and modern living room with a comfortable seating area and a TV for family movie nights. The fully equipped kitchen includes all the essentials needed for extended stays, along with ample storage and counter space. The dining area features a large table perfect for shared family meals. A washer and dryer are available for guest use, offering added convenience throughout your stay. brbrThe primary bedroom includes a King bed, walk-in closet, and ensuite bathroom with a walk-in shower. A second bedroom also features a King bed, providing plenty of comfort for multiple couples. The third bedroom is ideal for children with twin-over-twin bunk beds. All guests share access to a hallway bathroom with a walk-in shower. brbrRoom Details br-Primary Bedroom: King bed, ensuite bathroom with walk-in shower br-Second Bedroom: King bed br-Third Bedroom: Twin over Twin Bunk Beds brbrLocated just a short walk from Siesta Key Beach and Siesta Key Village, this home offers convenient access to island dining, boutiques, coffee shops, and entertainment. Guests enjoy a peaceful canal front setting, private heated pool, outdoor dining, and space for up to 3 parked vehicles. The home is dog friendly with prior approval and fee. brbrWith its private pool, canal front setting, refreshed interiors, and excellent proximity to Siesta Key Beach and Village, Coastal Charm by Tropical Sands Accommodations is the ideal choice for extended island living. Book your stay today and enjoy the best of Siesta Key! brbr- brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Tropical Sands Accommodations Rental Policies for full details. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. brbr3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

3

Bed

2

Bath

8

Sleeps

$1176.91

/ Nightly

Private Vacation Home

Tropical Siesta Key Getaway | Heated Private Pool + Fire Pit | 4BR Sleeps 10 | Minutes to Siesta Beach & Village!

Siesta Key, Florida, United States

This home is proudly managed by Beach Life Rentals & Sales. We offer flexible booking options—send us a message and we’ll do our best to accommodate your travel plans.brbrEscape to paradise at this beautifully appointed 4-bedroom, 3.5-bath vacation home in the heart of Siesta Key! With over 2,600 sq. ft. of indoor living space and a resort-style outdoor oasis, this family-friendly retreat is perfect for guests looking to relax, explore, and enjoy the island lifestyle. Nestled just outside Siesta Key Village, you`ll be minutes from white-sand beaches, local boutiques, waterfront dining, and family-friendly fun. Whether you`re floating in the private heated pool, unwinding by the fire pit, or taking a short stroll to any to the local White Sand beaches this home has everything you need for a laid-back, island retreat!brbr ️ Sleeping Arrangements:br- Primary Suite: King bed + private ensuitebr- Guest Room 1: Queen bedbr- Guest Room 2: Twin beds (2 twins)br- Lower-Level Bunkroom: Full over Twin bunk beds (4 beds total)brbr Bathrooms:br- 3 full bathsbr- 1 half bathbrbr Home Highlights:br- Private heated poolbr- Fire pit & BBQ grillbr- Screened-in front porchbr- Fully equipped kitchen (microwave, oven, stovetop, dishwasher)br- High-speed Wi-Fi & Smart TV`sbr- Washer & dryerbr- Central Air conditioningbr- Ample indoor & outdoor seatingbr- Professionally landscaped yardbrbr Nearby Attractions & Local Favoritesbr- Siesta Key Beach: World-renowned White Sand Beach known for its powdery quartz sandbr- Shell Beach: A hidden gem for shelling and sunsetsbr- Crescent Beach: Less crowded and ideal for familiesbr- St. Armands Circle: Upscale shopping, dining, and galleriesbr- Downtown Sarasota: Arts, theaters, and waterfront diningbr- Lido Beach: Great for swimming and people-watchingbr- The Ringling Museum: Art, history, and beautiful gardensbr- Mote Marine Laboratory & Aquarium: Hands-on marine fun for all agesbr- Siesta Key Marina Boat rentals: Dolphin tours, fishing charters, & more!br- The Legacy Trail: Scenic biking and walking trailbr- Turtle Beach: Quieter, nature-focused beach on the south end of the islandbrbr☀️ Dining Nearby:br- Gilligan’s Island Bar & Grill – Casual eats & live musicbr- Siesta Key Oyster Bar (SKOB) – Fresh seafood & happy hourbr- The Old Salty Dog – Island classic with waterfront viewsbr- Summer House Steak & Seafood – Upscale Island diningbr- Sun Garden Café – Local brunch favoritebrbr Good to Know:br- Minimum age to rent: 25br- Children are welcomebr- No pets allowedbr- No smoking or eventsbr- Check-in: 4:00 PM | Check-out: 10:00 AMbrbrWhether you’re planning a week of beach hopping and boating or just want to unwind by the pool with loved ones, this home offers the perfect mix of relaxation, adventure, and island charm. Book today with Beach Life Rentals & Sales and let the beach life begin! ☀️ brbrP.S. - Don`t forget to ask about our add ons! Concierge and airport shuttle services, boat rental referrals, and much more! Beach Life Rentals & Sales is your only true one-stop-shop for the total Island Vacation Experience! brThis is a smoke-free home. No smoking of any substance, including vaping. Smoking is allowed outside only. Please keep the property clean and tidy during your stay. An additional cleaning fee may be charged if the property is left excessively dirty. Please remember to turn off all lights, lock all doors and windows before leaving the property. We understand that sometimes accidents happen! Should you break anything, please let us know. Please do not take blankets, sheets or bath towels from the house to the beach. Please keep all garbage and recycling inside the provided totes during your stay. Please do not tamper with any of the pool/spa heating or filtering equipment.brbrRESPECT OUR NEIGHBORS PLEASE, QUIET TIME BEGINS AT 10PM. IT IS PERFECTLY FINE TO BE OUTSIDE HAVING A CONVERSATION, BUT NO LOUD MUSIC, SHOUTING, ETC. brbrExterior Landscaping lights come on automatically at dusk and shut off at dawn. The pool lights are controlled by a small white remote in the master bedroom window by the closet. Please do not leave pool lights on during the day. Never remove the pool light remote from its location. brbrGARBAGE/RECYCLE cans at the end of the driveway must be out by 7AM on MONDAY morning. Please be so kind as to put it by the road at the south end of the Driveway. As our designated pick up day is midweek, we thank you in advance for having to move someone else’s garbage as they will be doing the same favor for you the following stay. Please face the open lid side toward the street and have them approximately three feet off the road and separated by THREE feet each. The truck is automated so they are a little militant on this!brbrThe golf cart and a sea kayak in the garage ARE NOT FOR GUEST USE AND ARE NOT INSURED FOR ANY GUEST USAGE. GOLF CARTS AND BIKE RENTALS ARE AVAILABLE IN THE VILLAGE. THERE MAY ALSO BE A VEHICLE OR TWO IN THE CRUSHED SHELL DRIVEWAY. THESE ARE PERSONAL VEHICLES. brbrTHE MAIN PAVER DRIVEWAY IS ENTIRELY FOR YOUR USE DURING THE STAY AND FITS 4 VEHICLES COMFORTABLY. THERE IS ALSO A SMALL CRUSHED SHELL SECTION BY THE FRONT DOOR THAT MAY BE USED AS WELL FOR BIKES, GOLF CART RENTAL, ETC. brbrTHE garage refrigerator IS ONLY FOR HOMEOWNER USAGE. THERE ARE ALSO A FEW GRAY BASKETS ON THE UPPER SHELF IN THE MASTER CLOSET THAT CONTAIN SOME OWNER ITEMS. THEY ARE OUT OF YOUR WAY. THERE ARE TWO LOWER DRAWERS IN THE MASTER BATHROOM THAT ALSO CONTAIN SOME OWNERS ITEMS. brbrALWAYS PUT ALL GARBAGE CANS AND RECYCLING BIN OUT AT END OF DRIVEWAY UPON DEPARTURE, REGARDLESS OF DEPARTURE DAY.brbrNO PARKING ON LAWN EVER. *PLEASE NOTE WE DO KEEP A VEHICLE HERE IT MAY BE IN THE CLAMSHELL DRIVE.*brbrNO REARRANGING OF FURNITURE/MOVING FURNITURE BETWEEN ROOMS- BOTH INSIDE AND OUTSIDE.brbrWe respectfully ask guests to replace what they found in the house, usually at least a few pods for the dishwasher, at least a partial roll of paper towel and a few rolls of TP to get the next guests started upon arrival.brbrDO NOT FLUSH ANYTHING EXCEPT TOILET PAPER IN ANY TOILETS!!!!!!brLOWER LEVEL TOILET: YOUR NUMBER 2 IS OUR NUMBER 1 PRIORITY…PLEASE DO NOT USE THE LOWER LEVEL TOILET FOR YOUR NUMBER 2! brbrNO SMOKING INSIDE THE HOUSE OR NEAR ANY OPEN WINDOWS PLEASE!!!! $500 FEE WILL BE ASSESSED FOR SMOKING INSIDE THE HOUSE.brbrPlease keep the grill and grilling area tidy, do not leave wet towels anywhere inside, and do not touch the pool controls ever.brbrThe pool is set to cycle throughout 24 hours. The Pool temp is set to 82.brDEPENDING ON PUMP CYCLES THERE MAY BE A FLUCTUATION OF SEVERAL DEGREES BASED ON COOLER NIGHTS. brbrPLEASE LEAVE THE HOSE WHERE IT IS FOR POOL REFILL, THERE IS AN AUTOMATIC FILL CONTROL. IF YOU NEED TO WASH OFF SAND, SIMPLY PRESS THE BUTTON ON THE UNIT TO TURN ON, PRESS AGAIN TO TURN OFF, RETURN HOSE TO WHERE YOU FOUND IT. DO NOT SHUT OFF THE WATER AT THE FAUCET (IT IS THE RED HANDLE AND SHOULD REMAIN IN THE OPEN POSITION).brbrPlease feel free to use the skimmer net to remove any leaves, etc during your stay. The pool is serviced every Thursday around mid morning. brbrTHE POOL TV MUST BE COVERED EVERY NIGHT. PLEASE DO NOT LEAVE IT EXPOSED. YOU NEVER KNOW WHEN A POP UP SHOWER OR STORM MAY HAPPEN.brbrSTAY EXIT PROCEDUREbrPlease ensure all doors and windows are closed and locked upon exit of your stay. Please also ensure all pots and pans have been put away. Please make sure you run the last load in the dishwasher as you leave as well. Please leave all towels and bedding in the laundry basket/floor located on the top floor near the washer/dryer. If you could be so kind as to start at least one load of laundry upon your departure that would be greatly appreciated.brbrPlease make sure ALL thermostats are set to 76 degrees upon departure. There is a Thermostat on the main level, a thermostat on the top level at the top of the stairs and a remote for the basement unit. NEVER PUT UNITS LOWER THAN 72 DEGREES AS THEY CAN FREEZE WITH OUR SEASONAL HIGH HUMIDITY.brbrWe also ask that you do not leave any pamphlets, brochures, or magazines behind as well. We try to keep the house fairly clutter free for guests. brbrPlease make sure you also pick up any outside debris (plates, cups, etc). brbrPLEASE REPORT ANY DAMAGE IMMEDIATELY. IT IS A MUCH EASIER PROCESS TO GO THROUGH FOR BOTH PARTIES. PLEASE DON’T HAVE US FIND SOMETHING AFTER YOU LEAVE THAT MAY IMPACT THE NEXT GUESTS EXPERIENCE. YOU ARE RESPONSIBLE FOR ANY DAMAGE BOTH INSIDE AND OUT. brbrI FULLY ACKNOWLEDGE THAT THERE IS A POOL ON THE PROPERTY THAT DOES NOT HAVE A LIFEGUARD ON DUTY. I FURTHER ACKNOWLEDGE THAT ALL PEOPLE WITHIN THE GROUP STAYING AND/OR DAY VISITORS HAVE BEEN INFORMED BY THE RENTING PARTY THERE IS NO LIFEGUARD ON DUTY. I FURTHER ACKNOWLEDGE THAT NO UNDER THE AGE OF 14 IS ALLOWED TO BE AT THE POOL UNATTENDED BY AN ADULT AND I (RENTER AND ALL PARTIES BOTH STAYING AND VISITING ) HOLD THE HOMEOWNER HARMLESS OF ANY ACCIDENT AND DEATH RELATED TO THE POOL.

Bed

Bath

Sleeps

$645.26

/ Nightly

Private Vacation Home

Stunning Dog-Friendly Pool Home Close to SK Village and Beaches

Siesta Key, Florida, United States

Experience the epitome of relaxation and coastal charm at our newly renovated Siesta Key vacation home. Nestled in a serene neighborhood, this stunning 3-bedroom, 2-bathroom retreat is a haven of tranquility, exuding a contemporary coastal vibe with its soothing light blue and white hues that perfectly complement the surrounding lush landscaping. With its thoughtful furnishings and impeccable design, this home promises to make your getaway truly unforgettable.brbrProperty Highlightsbr-Open living area with French doors leading to a covered lanaibr-Wood-burning fireplace and flat-screen TV for cozy eveningsbr-Saltwater pool with loungers, outdoor dining table, and extra seatingbrbrPrimary Bedroombr-King bed, flat-screen TV, ensuite bathroom with spacious showerbr-Attached sunroom with desk, chair, private patio, and outdoor showerbrbr2 Guest Bedroomsbr-Each with queen bed and flat-screen TVbr-Shared bathroom with shower/tub combobrbrQueen Sleeper Sofabr-Pull out sofa to accommodate extra guests brbrbrAmenitiesbr-Beach gear providedbr-Fully fenced yard for privacy and petsbr-0.5 miles to Shell Beachbr-1 mile to public beach access & Siesta Key Villagebr-10-minute drive to Downtown Sarasota for dining, shopping, and culturebrbrThe Beauty of Siesta KeybrSiesta Key is a barrier island positioned between the Gulf of Mexico and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids. brbrThe Siesta Key Village offers a wide selection of shops, cafes, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate.

3

Bed

2

Bath

8

Sleeps

$1056.63

/ Nightly

Private Vacation Home

Two Homes with Shared Backyard, Perfect Rental for Groups - Village Time

Siesta Key, Florida, United States

Village Time by Siesta Key Luxury Rental PropertiesbrHome in Sarasota, FLbrbrWelcome to Village Time, a terrific choice for multi-family groups booking accommodation together, as each can enjoy their own separate space while staying close. Offering a total of six bedrooms, six full baths, and two half baths in two unique living areas, this home is a quick walk to Florida's prettiest beach and near Siesta Key village, which offers a wide variety of restaurants and shops. brbrHighlights br• Two separate living spaces perfect for family reunions and large groupsbr• Less than a 5-minute walk to the beach br• Two pools with in-ground spasbr• BBQ Grillsbr• Dog friendly with approval and additional feebr• Ping Pong tablebr• Foosball tablebr• Near Siesta Key Village restaurants and shopsbrbrOn each unit's main living floor are coastal living rooms with plush sofas and fully equipped kitchens, including utensils, pots, and pans, and they have their own dining tables and bar-top seating. Additionally, each unit has a half bath and a washer and dryer. brbrThis beautiful duplex offers six bedrooms, six full baths, and two half baths. Each side has three bedrooms and three- and one-half baths. A primary bedroom with a King bed, a balcony overlooking the sparkling pool, and an ensuite bathroom with a walk-in shower. The King guest bedrooms have tasteful beach décor, a balcony, and an ensuite bathroom with a walk-in shower. Across the hall is the bunk bedrooms, which are appointed with two bunk beds, a TV, and an ensuite bathroom with a shower and tub combo. brbrRoom Details brIsland Time West br-Primary Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower br-Second Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with walk-in shower br-Third Bedroom, 3rd floor: Two Full over full bunk beds and ensuite bathroom with a shower and tub combo brIsland Time East br-Primary Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower br-Second Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with walk-in shower br-Third Bedroom, 3rd floor: Two Full over full bunk beds and ensuite bathroom with a shower and tub combo brbrEnjoy the Florida sunshine in the comfort of either backyard that features a dazzling pool and spa and open the gates to create a sense of togetherness. Guests can sunbathe and read their favorite book on one of the loungers. Complete the evening with a freshly grilled BBQ meal and share it at the covered picnic table, then head to the ground-level game rooms for some friendly rounds of Ping Pong and Foosball.brbr-brThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details.brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$348.83

/ Nightly

Private Vacation Home

BRING YOUR BOAT! Gorgeous Canal Home with Pool near the Beach

Siesta Key, Florida, United States

Treasure on the Canal by Siesta Luxury Rental Properties br brWelcome to Treasure on the Canal, a luxurious waterfront, Tuscan contemporary retreat with three bedrooms and two full baths, plus two half baths. Featuring a private pool and spa with stunning canal vistas, this home offers seamless indoor-outdoor living just moments from Siesta Key Beach and vibrant Siesta Key Village. With a private dock accommodating boats up to 25 feet, and a host of outdoor amenities including kayaks and a built-in grill, this property is ideal for families, water enthusiasts, and large groups seeking a relaxing yet adventurous escape!br brHighlights br• Canal front home – Bring your boat! br• Private dock that can accommodate up to a 25 ft boat br• 3 Bedroom / 4 Bathroom br• 2 Kings, 1 Queen, 2 Twin beds br• Two kayaks and life jackets  br• Private heated pool and in-ground spa br• Screened-in lanai, Built-in grill br• Dedicated workspace br• 15-minute walk to Siesta Key Beach’s br• Short stroll to Siesta Key Village shops and dining br• 4 Parking spaces br brEnjoy outdoor living at its finest with a private dock perfect for boat trips or water sports, a heated pool and spa, and a screened-in lanai with a bistro table for dining outdoors. The outdoor kitchen with built-in grill and sink makes hosting effortless. Kayaks and life jackets are included for waterfront exploration, providing endless adventure options. br brThe spacious, open concept living area invites relaxation with a modern seating arrangement and a smart TV. The formal dining table and sleek wet bar with a wine fridge make entertaining easy. The fully equipped kitchen features upscale cabinetry and stainless steel appliances, supported by a cozy kitchen table for intimate meals. Large windows and sliding doors open to the screened lanai, blending indoor comfort with outdoor breezes. br brThe primary suite on the first floor offers a king-sized bed, a luxurious ensuite with dual vanities, a walk-in shower, and a soaking tub, creating a spa-like retreat. Upstairs, the two guest bedrooms are furnished with plush bedding, including a king and a queen bed and easy access to a hall bath with a walk-in shower and a tub. And the bonus room with two twin beds provides you with a private balcony. brbrRoom Details br• Primary Bedroom (1st floor): King bed, ensuite with walk-in shower and soaking tub  br• Guest Bedroom (2nd floor): Queen bed br• Guest Bedroom (2nd floor): King bed br• Bonus Room (2nd floor): Two twin bedsbr brGuests enjoy a washer and dryer, outdoor seating, kayaks, a private dock, and scenic water views. Located close to Siesta Key beaches, shops, and waterfront dining, Treasure on the Canal offers a perfect balance of outdoor adventure and relaxed coastal luxury.br brBook your stay at Treasure on the Canal today for a Gulf Coast vacation filled with water based adventures, resort style amenities, and unforgettable sunsets. Whether kayaking, lounging by your private pool, or exploring Siesta Key Village, this home provides everything you need to make your island retreat extraordinary. Reserve now to start your memorable escape! br brbr- brThis home is managed by Siesta Key Luxury Rental Properties.  brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.brbrThis property does not allow pets of any kind.  brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis property is equipped with exterior security cameras for safety purposes. A doorbell camera is located at the front entry, and an additional camera monitors the side of the home near the pool equipment. These cameras do not face any private or recreational areas and do not intrude on guest privacy. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details.  brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without a refund.

3

Bed

2

Bath

8

Sleeps

$1104.87

/ Nightly

Private Vacation Home

Casa De Mayo on Siesta Key

Siesta Key, Florida, United States

Summary:brbrWelcome to Casa De Mayo, a private waterfront retreat close to Siesta Village + the powder-soft sands of Siesta Key Beach. Behind private gates, enjoy a lush yard with a sparkling pool, screened lanai with remote open/close, and direct canal access for kayaking or paddleboarding. This 3-level home has a Game Room, a luxurious primary suite with office, open-concept living, and an oversized bunk room—perfect for families and groups seeking laid-back island luxury. Bring your boat!brbrbrbrThe Neighborhood:brbrOn a canal with a short walk to the village.

4

Bed

3

Bath

14

Sleeps

$587.01

/ Nightly

Private Vacation Home

Two Connected Villas, Walk to Beach, Nightlife & Pool

Siesta Key, Florida, United States

Why You’ll Love It!br------------------------brJust a short 2-minute walk to Siesta Key Beach, the newly renovated Siesta Treasure delivers the best of Siesta Key. Nestled in quiet cul-de-sac, this duplex villa is located just steps from the pristine white beach, heated pool, top restaurants and local fish market, shopping, and activities including bike, kayak, and paddle board rentals. brbrEnjoy the laid-back beach lifestyle in comfort, with thoughtful amenities provided for your stay. Perfect for guests seeking a peaceful island retreat with all the charm and convenience of a top-tier location. Unpack, relax, and enjoy Siesta Key!brbrbrConvenient Amenities Included! br-------------------------------------brSand-resistant soft Turkish beach towels are provided for all guests, as well as beach chairs, umbrellas, beach carts and a cooler! Enjoy clean plush bath towels as well as a starter pack of vacation essentials which includes soaps, shampoo, conditioner, as well as locally roasted coffee for our guests so you can begin your stay right away! A starter set of dishwasher and laundry detergent tabs are also provided as well as garbage bags and a roll of paper towels. brbrbrAbout the Homebr------------------------brThis newly renovated duplex offers step-free access throughout the home. Both units #3 and #4 are connected through a locked access door in the laundry room. Each unit features a fully equipped and stocked kitchen with cooking essentials and appliances, 2 bedrooms with fresh quality linens and pillows, 1 bathroom with a shower tub combo and plush towels, a living area with a Smart TV and Amazon Prime service, and a dining area with seating for four. brbrThe primary bedroom features a queen bed, while the secondary bedroom includes two twin beds – each room includes extra linens and pillows. There is also a comfortable cot provided for an extra guest if needed. brbrThe laundry room is shared access for both units with an additional access door to the private fenced-in backyard. The large private backyard includes a patio seating area with umbrella for shade and a gas grill with propane, as well as plenty of beach essentials for your stay! There is also an outdoor shower to rinse any sand after a day at Siesta Key Beach. br brbrBeach and Pool Just Steps Away!br-----------------------------------brSiesta Key Beach is just a two minute walk away! The pool is heated and just steps from the villa and beach. We will provide all access codes and instructions after your booking is confirmed. brbrbrParking and Access br--------------------------brLocated on the ground floor there is step-free access throughout the villas. Parking is conveniently available right outside for up to two cars.brbrbrOther Things to Notebr--------------------------------br• Prime location in the heart of Siesta Key.br• Heated community pool just steps away for year-round relaxation.br• Walking distance to top restaurants, bars, grocery, fish market, and local shops right across the street.br• Close to bike and kayak rentals, beach gear shops, and island activities, making it easy to explore without a car.br• High-quality bedding, linens, and plush towels for a restful stay.br• Gas grill for cookouts and outdoor dining table for 4 with umbrellabr• Sun loungers for relaxing in the shade or sunshinebr• Outdoor shower for sandy feet and beach gearbr• Front patio with outdoor seating—perfect for sunset views and Gulf breezes.br• Beach chairs, umbrella, wagon, cooler, towels, pool floats—everything you need for easy beach days.br• High-speed Wi-Fi for remote work or streaming.br• Air conditioning and ceiling fans for cool, comfortable living.

Bed

Bath

Sleeps

$1072.41

/ Nightly

Private Vacation Home

Large Home, Private Pool, Arcade Lounge and Beach

Siesta Key, Florida, United States

Exclusive Amenities Include:br• Private Heated Poolbr• Outdoor Grill with Lounge & Dining Areasbr• Pool Chassis and Umbrellasbr• Arcade Games, Connect 4, Foosball & Cornholebr• Multiple Indoor Living Spacesbr• Theater Room & Game Loungebr• In-Home Laundry with Washer & Dryerbr• Smart TVs & High-Speed WiFibr• Fully Equipped Kitchen and Coffee Makers, Dishwasherbr• Beach Gear: Chairs, Towels, Cooler, Wagon Caddybr• Starter Packs: Bathroom Toiletries & Kitchen Home Essentialsbr• Enhanced Cleaning ProtocolsbrbrThe spacebrCase Sea Esta | Private Pool, Arcade and Movie Theatre Lounge, 0.8 Miles to Siesta Key BeachbrbrWhy You’ll Love This HomebrStep into a sun-kissed Siesta Key escape where island charm meets elevated comfort. Float in your private heated pool, rinse off under the outdoor shower after the beach, and unwind in airy, coastal interiors made for slow mornings and easy nights. With space to spread out, beautiful bedrooms, and cozy gathering spots inside and out, this home is designed for laughter, connection, and those unforgettable “we should stay forever” moments.brbrPerfect ForbrUpscale families, groups traveling together, and beach and luxury lovers seeking a centrally located home designed for an exceptional vacation experience.brbrImagine ThisbrWake up to soft morning light and coffee in hand. Slip into the warm heated pool before the day begins, then head to Siesta Key Beach for white sand and turquoise water. Come home, shower off the salt air, and sink into the shade with a book while the grill heats up. As the sun sets, share dinner under the lights, linger by the firepit, and end the night with a movie, a glass of wine, and that calm island feeling you don’t want to leave.brbrWhere You’ll SleepbrBedroom 1: King Bed, Ensuite Bath with Walk-In Shower, TVbrBedroom 2: King Bed, Hall Access Ensuite with Bath, TVbrBedroom 3: Queen Bed, Hall Access Ensuite with Walk-In Shower, TVbrBedroom 4: Queen Bed and another Queen Bed (2), Hall Access Ensuite with Walk-In Shower, TVbrbrExplore the Areabr• 0.7 Miles to Siesta Key Main Beach Access – Sun, Sand, and Sugar-White Shoresbr• 0.6 Miles to Siesta Key Village – Coffee Shops, Ice Cream, Dining, and Boutiquesbr• Short Ride to St. Armands Circle – Upscale Shopping and Restaurantsbr• Walkable Residential Streets – Safe and Family-Friendly NeighborhoodbrbrNeed to Know - This pool is heated whenever you like. This home has stairs. If any member of your party has difficulty with stairs, please reach out to discuss. Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high speed WiFi. For added security and peace of mind, exterior cameras are installed at the front of the home. No smoking, no pets, and no parties allowed. There is a 1 rental per 30 day period, per Sarasota, FL ordinance, reach out for more information. Reservation must follow under the accordance of the Sarasota County code regulations.

Bed

Bath

Sleeps

$916.13

/ Nightly

Private Vacation Home

Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach and Village! - Casa Siest

Siesta Key, Florida, United States

Casa Siesta by Siesta Key Luxury Rental Properties is a beautifully designed three-bedroom, three-bathroom private pool home, ideal for families and friends seeking a refined Siesta Key vacation rental just steps from the beach. Located approximately a 1-minute walk to Siesta Key Beach, this retreat offers an exceptional blend of walkable beach access, private outdoor amenities, and suite style accommodations. Guests are also within a short 5-minute walk to the shops, restaurants, and nightlife of Siesta Key Village. With a private pool and spa, rooftop deck with beach views, and multiple outdoor living spaces, Casa Siesta delivers a relaxed yet elevated island experience. brbrHighlights br• 1-minute walk to Siesta Key Beach br• 3 Bedrooms / 3 Bathrooms br• 3 King beds, 1 Twin trundle bed br• Private pool and in-ground spa br• Rooftop deck with beach views br• Walk to Siesta Key Village shopping and dining br• BBQ grill and outdoor seating br• Professional Linen Program br• Parking for 2 vehicles brbrCasa Siesta’s outdoor spaces are thoughtfully designed to enhance every moment of your stay. The private front courtyard features a sparkling swimming pool and in-ground spa surrounded by lounge chairs, creating an inviting space to unwind after beach days. The rooftop deck, accessible from the second floor, is one of the home’s most memorable features. From here, guests can enjoy views toward the beach and take in colorful sunsets, making it a favorite gathering spot in the evenings. A BBQ grill and outdoor seating areas allow guests to enjoy meals and conversation outdoors throughout their stay. brbrInside, Casa Siesta offers a bright and welcoming great room designed for comfort and connection. The living area features an oversized sofa and loveseat with a television, providing a cozy space for movie nights or downtime between beach outings. The chef style kitchen is fully equipped with stainless steel appliances, ample counter space, and all essential cookware and utensils. A modern dining table offers comfortable seating for shared meals, while the covered patio extends the dining space outdoors and includes a television for casual entertainment. brbrThe primary bedroom is located on the second floor and serves as a private retreat, featuring a king bed, private balcony access, a walk-in closet, and an ensuite bathroom with dual vanities and a walk-in shower. This space offers both comfort and privacy after full days on the island. The second bedroom, also on the second floor, includes a king bed, private balcony, and an ensuite bathroom with a walk-in shower. The third bedroom is located on the first floor and features a king bed and an ensuite bathroom with a walk-in shower, making it ideal for guests who prefer easy access without stairs. A second-floor loft area provides additional flexibility with a twin trundle bed, television, and desk area, perfect for children or extra sleeping arrangements. brbrRoom Details br-Primary Bedroom (2nd Floor): King bed, private balcony, ensuite bathroom with walk-in shower br-Second Bedroom (2nd Floor): King bed, private balcony, ensuite bathroom with walk-in shower br-Third Bedroom (1st Floor): King bed, ensuite bathroom with walk-in shower br-Loft (2nd Floor): Twin trundle bed brbrThis home includes a full laundry room located off the garage for guest convenience. Located just steps from Siesta Key Beach, guests can enjoy daily beach walks, swimming, and sunsets over the Gulf. The home’s proximity to Siesta Key Village allows easy access to local restaurants, cafes, boutique shopping, and island nightlife, creating a well rounded vacation experience. brbrIf you are searching for Siesta Key luxury rentals with walkable beach access, private pool living, and close proximity to Siesta Key Village, Casa Siesta by Siesta Key Luxury Rental Properties is an exceptional choice. Enjoy effortless island living just steps from the sand and moments from dining and entertainment. Book your stay today and experience the best of Siesta Key! brbr - brThis home is managed by Siesta Key Luxury Rental Properties brbrThis property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment. brbrThis property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property does not allow pets of any kind. brbr2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$796.65

/ Nightly

Private Vacation Home

Island Sol: Secluded 4 BR Paradise with Salt Water Pool, Walk to the Village

Siesta Key, Florida, United States

Contact the host to inquire about discounts for longer stays! We offer 25% off stays longer than 14 nights, 30% off 21 nights, and 35% off of 28 nights or more. The 28 night discount shows in the listing, but please inquire for 14 or 21 night discounts.brbrThis 4 bedroom, 3.5 bathroom serene, lakefront oasis with a private pool is a short walking distance from Siesta Key Village. With a bathroom on each of the 3 floors and 4 king, 3 twin, and 1 full beds, this home sleeps 13 and is the perfect retreat for multiple families, 4 couples, or a multigenerational family vacation.brbrOutside the home you will find several areas of enjoyment around the property including a lakefront firepit, a private, heated salt-water pool, a covered lanai area with a ping pong table and a large HDTV and seating area, and a bike storage area. If you enjoy nature, we recommend getting biodegradable turtle food to throw into the lake to see the wildlife up close. brbrInside, the home is laid out over three stories with a full bathroom on each level for optimum privacy. In the lower level, which has it's own separate entrance, there is a bedroom with a king sized bed and additionally a full bed in the laundry room/kitchenette just outside the bedroom. This level also houses a large washer and dryer, a Keurig, a full sized refrigerator, outdoor dining supplies, and a sink/countertop area for food prep. The second level of the home consists of a full sized kitchen, dining room, living room with a large HDTV, an enclosed porch that overlooks the lake, a half bathroom, and the primary bedroom with a full ensuite bathroom. The third level of the home has two bedrooms, each containing a king sized bed, and a shared full bathroom. All bedrooms have a large HDTV.brbrThe home also has several beach cruiser bikes and two closets full of beach and pool accessories including a wagon, beach chairs, sand toys, pool toys, and many floaties. The driveway has room for 3-4 cars (if you don't mind parking each other in).brbrThe free Siesta Breeze trolley picks up within a block of the house and loops between downtown Sarasota and Turtle beach on the south side of the island. You can ride the trolley a few blocks to get to the village or beach access points or easily walk or ride bikes. brbrYou will not regret staying in this tropical paradise just minutes away from Siesta Key Beach and Siesta Key Village!

Bed

Bath

Sleeps

$346.05

/ Nightly

Private Vacation Home

Sea Angel - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Sea Angel | 400 Ft to Beach + Dog Friendly + Shared Patiobrbr Why You'll Love This HomebrPerched on the top left corner of CJ's on Siesta, Sea Angel offers cozy privacy and bright natural light just steps from Siesta Key Beach. With fresh interiors, a king suite, and a relaxing outdoor patio shared with just five other units, it's the ideal beach hideaway for couples or small families.brbr ‍ ‍ Perfect ForbrCouples, solo travelers, or a small family seeking a walkable, pet-friendly retreat near the beach and Village fun.brbr ️ Imagine ThisbrStart your morning with a fresh cup of coffee as the sunlight pours through your corner-unit windows. Slip on sandals and stroll just 400 feet to the world-famous sands of Siesta Key Beach. After soaking up the sun, stop by Siesta Key Village for a fish taco or cold drink, then return to your tranquil unit to unwind. Fire up the shared grill, stretch out on a lounger under the palms as the evening breeze rolls in.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Second Floor (Top Left Unit), TVbr• Living Area: Modular Sleeper Sofa, Open Concept Living Room, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Beach (400 feet)br• 0.1 miles to Siesta Key Village – Walkable to Restaurants, Shops, and Nightlifebr• Tucked in a Vibrant, Coastal Neighborhood with Local Energy and Beachside Charmbr• Easy Access to Water Sports, Ice Cream Spots, and Sunset Strollsbrbr⌛ Don't Wait—This Home Books FastbrYour stay at Sea Angel includes peace of mind with a 6-hour deep clean and 35-point inspection before every arrival. Bonus: Furry friends welcome! This unit allows 1 dog (up to 25 lbs) with an applicable pet fee.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. One designated parking space is available. Free High-Speed WiFi in the unit. Shared on-site laundry available. One dog allowed (max 25 lbs) with a pet fee. If any guest has difficulty with stairs, please contact us for alternative accommodations. Your listing is part of a multi unit complex and is a distinct unit—with its own private entrance, kitchen, and living areas—with no interior connection. As a multi-unit complex, it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). Contact us directly for more information regarding any shared space for this vacation home.

1

Bed

1

Bath

4

Sleeps

$2497.38

/ Nightly

Private Vacation Home

CJs - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key, Florida, United States

CJ's on Siesta | 400 Ft to Beach + Shared Patio & Grillbrbr Why You'll Love This HomebrSteps from Siesta Key Beach and nestled in the heart of the Village, CJ's on Siesta offers the rare flexibility of six private, stylish units all in one place. A spacious shared patio with chaise loungers, table with chairs, and grill sets the stage for unforgettable moments between dips in the ocean and sunset cocktails.brbr ‍ ‍ Perfect ForbrMulti-family groups, wedding guests, reunions, or corporate retreats seeking connected-yet-private accommodations right by the beach.brbr ️ Imagine ThisbrWake up and sip coffee just 400 feet from the powder-soft sands of Siesta Key Beach. Everyone has their own space—each unit offering a king suite, cozy lounge with sleeper sofa, and full bath. Meet in the shared patio for morning plans under the palms, then stroll into Siesta Key Village for brunch or boutique browsing. Evenings bring beachside sunsets followed by BBQs on the grill, laughter on the chaise lounges, and starry-night chats in your private outdoor retreat.brbr Where You'll SleepbrEach of the 6 private units includes:br• Bedroom 1: King Bed, Ensuite Bath, First or Second Floor, TVbr• Living Area: Modular Sleeper Sofa, Shared Living Space, TVbr Note: All units are similar in layout. Three are on the first floor, three on the second, with shared interior walls.brbr Explore the Areabr• 0.1 miles to Siesta Key Beach (400 feet)br• 0.1 miles to Siesta Key Village – Dining, Shops, Nightlifebr• Walkable, Vibrant Coastal Neighborhood with a Laid-back Tropical Vibebr• Quick Access to Water Sports Rentals, Beach Yoga, and Casual Eatsbrbr⌛ Don't Wait—This Home Books FastbrCJ's on Siesta provides everything needed for effortless group travel. Your reservation includes peace of mind with a 6-hour deep clean and 35-point inspection prior to your arrival.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. 6 parking spaces available. Free High-Speed WiFi in each unit. Shared on-site laundry available to all guests. If any guest has difficulty with stairs, please contact us for alternative accommodations. This listing is a multi unit complex and has distinct units. Each of the six units has their own private entrance, kitchen, and living areas—with no interior connection. As a multi-unit complex, it could share a dividing wall, floor, and ceiling. As the entire complex the outdoor space is private. Contact us directly for more information regarding any shared space for this vacation home.

Bed

Bath

Sleeps

$565.82

/ Nightly

Private Vacation Home

Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village

Siesta Key, Florida, United States

Welcome to Siesta Sunset, a breathtaking beachfront rental home located right on the pristine shores of Siesta Key Beach. This gorgeous condo not only offers direct beach access but also stunning panoramic views of the Gulf of Mexico, ensuring your island getaway is nothing less than spectacular!brbrAs you step inside Siesta Sunset, you'll be greeted by the magnificent beach views that can be enjoyed from three different rooms, allowing you to soak in the beauty of the coastline throughout your stay. The spacious balcony offers a prime vantage point for witnessing breathtaking sunsets and provides a comfortable lounge space where you can relax and unwind while being mesmerized by the tranquil Gulf views.brbrSiesta Sunset features three bedrooms and two full baths, including a master bedroom for added privacy and comfort. With two king beds, one queen bed, and one twin bed, this home comfortably accommodates up to six guests. Linens are provided, ensuring a cozy and restful night's sleep for everyone.brbrFor your convenience, Siesta Sunset offers a starter pack of toiletry essentials, including shampoo, conditioner, hand/face soap, body lotion, and makeup wipes. A starter pack of home essentials, such as dish soap, a dish sponge, dishwasher tablets, laundry tablets, and cleaning wipes, is also provided. Beach towels, chairs, a cooler, and a caddy are available in the bottom-level storage space, ensuring you have everything you need for a day at the beach. And if you're in the mood for a delicious BBQ, a gas grill is conveniently located on the side of the building.brbrThe amenities at Siesta Sunset cater to your every need. Two private carports provide convenient parking options, and free WiFi and four HDTVs keep you connected and entertained throughout your stay. The gourmet kitchen includes regular and Keurig coffee makers, a dishwasher, a washer and dryer, and all the kitchen essentials you need to prepare meals with ease. A pellet ice maker adds a special touch, providing cool refreshments for those warm beach days. The kitchen effortlessly merges with the adjoining living room and dining area, creating an open concept design. This allows you to enjoy breathtaking views of the water while seated comfortably in the heart of the home.brbrWith Siesta Key Beach just steps away, you have the convenience of easily accessing the soft powdery sands, crystal-clear waters, and endless beach activities. Spend your days sunbathing, building sandcastles, or taking refreshing dips in the ocean. The direct beach access ensures that you can fully embrace the beach lifestyle and enjoy the soothing sound of the waves throughout your stay.brbrLocated less than 0.5 miles from Siesta Key Village, Siesta Sunset offers the perfect balance between beachfront tranquility and the vibrant energy of the village. Explore the charming shops, indulge in delectable dining options, and immerse yourself in the local culture. Whether you're seeking a lively nightlife scene or a leisurely stroll through the village, the close proximity makes it convenient to experience all that Siesta Key has to offer.brbrIndulge in the ultimate beachfront experience at Siesta Sunset, where stunning sunsets, direct beach access, and a prime location combine to create an unforgettable vacation. Book your stay today and experience the best of Siesta Key!brbrExclusive Amenities Include:br• Direct Beach Access with Panoramic Beach Views From 3 Roomsbr• Spacious Balcony With Breathtaking Gulf Views & Lounge Spacebr• Siesta Key Beach Just Steps Awaybr• Less Than 0.5 miles to Siesta Key Villagebr• 3 Bedrooms, 2 Full Baths (1 Master Bedroom)br• 2 King Beds, 1 Queen Bed, & 1 Twin Bed (Sleeps 6) with linens providedbr• 2 Private Carportsbr• Free WiFi & 4 HDTV'sbr• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Pellet Ice Makerbr• Beach Towels, Chairs, Cooler, & Caddy Provided - located in bottom level storage spacebr• Gas Grill - Located On Side Of Buildingbr• Enhanced cleaning protocols provided by our CottageClean Teambr• Island Shuttle Transportation AvailablebrbrSiesta Sunset can accommodate up to 6 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1)br• Bedroom # 2: King Bed (1)br• Bedroom # 3: Queen Bed (1) & Twin bed (1)brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrNEED TO KNOW: This home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the 1st floor covered parking area labeled PH. This unit is a 3rd floor unit with no elevator; however, if you need assistance bringing large items up the stairs, let us know and our team would be happy to assist! Contact us directly for more information regarding any shared space for this vacation home.

Bed

Bath

Sleeps

$2342.88

/ Nightly

Private Vacation Home

Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly ️☀️

Siesta Key, Florida, United States

Step into the luxurious embrace of Luxe Lagoon, where Siesta Key's charm blends seamlessly with unparalleled sophistication. This exclusive, 7-bedroom, 7-bathroom estate accommodates up to 20 guests and promises a vacation experience like no other—one where elegance and comfort meet every desire. Whether you're gathering with family, friends, or colleagues, Luxe Lagoon is the perfect haven for your getaway.brbrAs you enter the private backyard oasis, a tropical paradise unfolds. Surrounded by lush, swaying palms, the heated pool and spa invite you to unwind and immerse yourself in pure relaxation. For added enjoyment, the manicured putting green and ping pong table offer entertainment and leisure without ever leaving the property. A convenient half-bath is located on the first floor, ensuring easy access for all guests.brbrThe second floor welcomes you with lavish accommodations. Three king bedrooms, each with their own en-suite bath, offer a restful retreat for your group. The spacious kitchen area, with its sprawling island, 8-seat dining table, and 5 barstools, is perfect for meal prep and socializing. Cooking here is a joy with the top-of-the-line gas range elevating every culinary creation.brbrVenture up to the third floor, where comfort and style continue. Four beautifully appointed bedrooms include three king suites, each with en-suite bathrooms, and a charming bunk room featuring two sets of Full-over-Full beds—ideal for families or groups. The spacious living area, with ample seating and a sophisticated wet bar, opens onto a wraparound balcony with tropical views that instantly soothe the soul. Here, you'll hear the sound of the hot tub waterfall and the gentle rustling of palm leaves—perfect for unwinding after a day of adventure.brbrFor an elevated experience, take the spiral staircase up to the rooftop terrace, where panoramic views of Siesta Key Beach and Village await. Watch the sun set over the sparkling Gulf Coast and indulge in moments of tranquility that are uniquely Siesta Key.brbrLuxe Lagoon is more than a home—it's a luxury experience, where every detail has been carefully considered to offer you the ultimate vacation. From the stunning interior design to the lush outdoor spaces, this is a place where you'll feel deeply connected to the serene beauty of Siesta Key. Whether you're here for a relaxing retreat or an adventure-filled vacation, Luxe Lagoon delivers a blend of elegance, comfort, and unforgettable moments.brbrBook your stay at Luxe Lagoon today and make memories in this breathtaking Siesta Key paradise.brbrbrExclusive Amenities Include:br• Private Heated Pool & Spabr• Breathtaking Sunset and Partial Gulf Views on Rooftop Terracebr• Less than 500 ft to Siesta Key Villagebr• Less than a 3 Minute Walk to Siesta Key Beachbr• 7 Bedrooms (7 Master Bedrooms), 7 Full Baths, 2 Half Bathsbr• 6 King Beds & 2 Full Over Full Bunk Beds (Sleeps 20) with linens providedbr• Multiple Spacious Balconiesbr• Three Story Convenience Elevator for luggage, groceries and personal gearbr• Private parking for 2 vehicles in drivewaybr• Free WiFi & 11 HD Smart TV'sbr• Wolf / Subzero Kitchen Appliances, Regular & Keurig Coffee Maker, Dishwasher, Washer and Dryer, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Beach Towels, Chairs, Cooler, & Caddy Providedbr• Outdoor Lounge Area Includes Ping Pong, Wooden Bar with HD Smart TV, Dining Table, Gas Grill, & Poolside Showerbr• Enhanced cleaning protocols provided by our CottageClean Teambr •Island Shuttle Transportation Availablebr• Dog-Friendly with a Fee (1 dog up to 25lbs)brbrLuxe Lagoon can accommodate up to 20 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1) - Sleeps 2 - Private Bathroom 1br• Bedroom # 2: King Bed (1) - Sleeps 2 - Private Bathroom 2br• Bedroom # 3: King Bed (1) - Sleeps 2 - Private Bathroom 3br• Bedroom # 4: King Bed (1) - Sleeps 2 - Private Bathroom 4br• Bedroom # 5: King Bed (1) - Sleeps 2 - Private Bathroom 5br• Bedroom # 6: King Bed (1) - Sleeps 2 - Private Bathroom 6br• Bedroom # 7: Full Bunk Beds (2) - Sleeps 8 - Private Bathroom 7brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrPLEASE NOTE: This pool is heated from November 15th to April 15th.brbrThis home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.

Bed

Bath

Sleeps

$543.47

/ Nightly

Private Vacation Home

A Private Secluded Retreat In Great Neighborhood -Sleeps 8 Near Beach

Siesta Key, Florida, United States

This is a spacious, two story, 4 bedroom home with 3 master suites that have their own on-suite bathrooms. Two of these masters have king size beds and TV's, the other Master has a queen bed and a TV as well. The 4th bedroom has 2 twin beds and a TV with a Sony play station and games for the kids. There is also a small play area on the balcony for kids with books, chairs and toys to play with. The kitchen is very spacious newly remodeled with stainless steel appliances, a new stove and dishwasher. All kitchen utensils are supplied and all linens as well. The laundry is conveniently located on the second level with a brand new front load washer and dryer and a utility sink -beach towels are in the laundry room as well. The home also has an attached 2 car garage with pool toys, beach chairs, 4 bicycles, a surf board,fishing poles, tennis rackets, beach umbrella, and cooler as well as other items for your beach pleasure.brbr We also have a spacious patio/lanai with stairs leading to our wonderful lap pool! On the lanai and/or pool deck we have patio chairs, 2 recliners, a table and a BBQ grill for you to enjoy family time. br Come and make memories in our home..enjoy the Florida lifestyle and re-energize your mind and soul! We look forward to your stay!You can always reach us by calling 941 626 2625 for any other questions as well

Bed

Bath

Sleeps

$559.7

/ Nightly

Private Vacation Home

Stunning 3 Bedroom/ 3 Bath Adjacent to Siesta Key Beach Access!

Siesta Key, Florida, United States

Spend your vacation relaxing in this lovely 3-bedroom, 2.5-bathroom townhome. On the ground level, you will find covered parking for up to 2 cars, and storage. The second level hosts an open concept for the living room, dining, and kitchen areas. The spacious living room features rattan ceiling panels for a casual coastal vibe. The kitchen offers plenty of storage and stainless countertops. On this floor, you will also find a powder room and a balcony for enjoying the fresh island breeze. The 3 bedrooms and 2 full bathrooms are located on the third level. The master bedroom features a king and an area with two twins and privacy doors for separations. Located within walking distance to Siesta Key Village, this home is adjacent to beach access #10 – perfect for taking a trip down to Siesta Beach! br*This property is stairs only; all guests must have the ability to use stairs.brbrBedroom 1 – 1 King, 2 Twin beds, and 1 Twin TrundlebrBedroom 2 – QueenbrBedroom 3 – Two DoublesbrLivingroom – Queen Sleeper SofabrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolly - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25 br*To book a beachside managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security authorization Hold taken upon check-in. Amount: $1,000

Bed

Bath

Sleeps

$433.35

/ Nightly

Private Vacation Home

Pineapple on Siesta Key

Siesta Key, Florida, United States

Kick back and relax in this calm, stylish 3-bedroom, 4-full bathroom canal-front home, perfect for families or couples seeking a tranquil getaway. Just a short 5-minute walk away, you`ll find the vibrant Siesta Key Village, offering a variety of shops, restaurants, and entertainment. And, of course, you`re just minutes from Siesta Key Beach, consistently ranked as the #1 beach in the US! brBook your dream vacation today and experience the best of Siesta Key!`

Bed

Bath

Sleeps

$539.04

/ Nightly

Private Vacation Home

Zach’s Siesta Key Beach House|Pet Friendly| #1 Beach in USA

Siesta Key, Florida, United States

Take it easy at this mid-century modern peaceful Siesta Key Beach family & pet friendly getaway. 3 BD, 2 BA’s & 2 outdoor showers to wash off the sand after beach fun. Don’t forget to bring Fido! Hang out by the fire pit in the evenings while you grill out taking in the ocean air with a sky full of stars after an amazing day at America’s #1 beach. Enjoy the beach cruisers for morning coffee runs, sunset rides, live music, ice cream, shops or any of the amazing restaurants in Siesta Key village.brbrA very quiet, peaceful, relaxing family neighborhood across the street from the grand canal.brThe county picks up recycling and trash, Monday morning. There is one 96 gallon container for each for your use while staying. Please make sure each is positioned in front of the house on the sidewalk Wednesday evenings after dark.

2

Bath

6

Sleeps

Exceptional(25)

$869.11

/ Nightly

Private Vacation Home

Villa Castile | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Walk to Beach & Village!

Siesta Key, Florida, United States

️ Villa Castile | Private Heated Pool + Walk to Beach & Villagebrbr Why You'll Love This HomebrPicture yourself gathered poolside in your sunlit courtyard, the warmth of the heated pool inviting you to pause time. Just steps from Siesta Key Village and a short stroll to world‑famous Siesta Key Beach, Villa Castile blends sophisticated comfort with laid‑back island energy.brbr ‍ ‍ Perfect ForbrFamilies, multi‑family groups, or friends looking for space, privacy, and proximity—all with a touch of pet‑friendly flair.brbr ️ Imagine ThisbrYou awaken in the elegant king suite and sip morning coffee as dappled sunlight filters through courtyard greenery. Up for a beach day Grab chairs, towels, a caddy—and you're on the soft, white sand in under 10 minutes. Evening arrives and the screened lanai sets the stage for hearty grilled fare, laughter, and good wine. Later, you sink into plush sofas or cozy up by the fireplace—staying connected, relaxed, and utterly in the moment.brbr Where You'll Sleepbr• Bedroom 1: King Bed, ensuite bathroom, main floor, TVbr• Bedroom 2: King Bed, shared hall bath, second floor, TVbr• Bedroom 3: Two Queen Beds, ensuite bath, top floor, TVbrbr Explore the Areabr• 0.3 miles to Siesta Key Village – shops, restaurants, and lively island charmbr• 0.3 miles to Siesta Key Beach – powder‑white sand, turquoise surfbr• Walkable, vibrant, and deeply coastal—everything you need is right around the cornerbrbr⌛ Don't Wait - Homes this close to the beach with private heated pools book fast. Enjoy peace of mind with our CottageClean™ Program — a 6‑hour deep clean plus rigorous 35‑point inspection to welcome you into what feels like a brand‑new vacation home.brbr Need to Know - This home is part of a duplex — you'll have access only to the right‑side unit, including a private fenced backyard and heated pool. Pool jets are not usable by guests. The pool is heated November 15 – April 15. This unit has stairs, Contact us for questions about stairs, shared spaces, or pet policies.

3

Bed

3

Bath

8

Sleeps

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