Vacation Rentals By Owner In Siesta Key, FL

Extremely Private: -inspired elegant decor welcomes you to this secluded tropical getaway and makes you feel at home with a 120-foot-long boat dock directly on Little Sarasota Bay with plenty of dolphin and manatee activity. You won't even realize you are minutes away from a bustling city since the house sits back far from the road, you won't even hear the cars on the way to the beach, but you will hear the boats from the dock. Steps from the beach, complete with all the modern amenities and comforts of home, including a complete kitchen including a gas stove and new appliances, coffee bar, pantry and seating for 10. Outside you will find an amazing kitchen with grill, kitchen necessaties and a table seating 8 with sofa, wood fireplace and large screen tv. There are three bedrooms each with king mattresses ( two are master bedrroms). Each bedroom has their own bathroom. Extra bunk beds can be added with notice. Each bedroom has a smart Samsung large wall mounted tv. (12 person maximum) linens, and ceiling fans included in each bedroom. The family room comforatable seats 6-8 with a large tv. There are five (5) Samsung flat screen cable TVs and WIFI internet access, garage, three living levels with elevator, heated spa and pool overlooking bay, 120-foot fishing dock with underwater snook lights on the bay for best night fishing, yoga room with fitness equipment, free (2) bike - one is electric/ (2) kayak usage, (3) Stand Up Paddleboard (SUP) outdoor fireplace, horseshoes, lounge chairs, and two sets of washer/dryers. brFishing gear and additional bikes for rent. Free transportation is available at the end of the driveway. Additional guests can be accommodated at $25 per guest per night. We are less than a mile south of Crescent Village shops, restaurants and beautiful Crescent Beach. Also included in our home are linens, towels, toiletries (shampoo, conditioner, soap) as well as a pool towels. All the amenities of home because it is our home.

Siesta Key Our Mc-Masion Bayfront Home Steps from the World's Finest Beaches

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$626.05

Unparalleled Luxury at Casa Leone, Siesta Key's Hidden GembrWelcome to Casa Leone, your ultimate luxury getaway on Siesta Key. Located on the northern end of this iconic island, this stunning vacation home combines comfort, style, and convenience, making it the perfect destination for your beach vacation. Whether you're here to relax or explore, Casa Leone offers everything you need for an unforgettable stay.brbrSpacious, Elegant Interiors for Unmatched ComfortbrAs you step inside, you'll be greeted by an open-concept living area filled with natural light and designed for ultimate comfort. The first-floor living room, just off the pool, is the perfect place to unwind after a fun day at the beach, with plush sofas and a flat-screen HDTV for cozy movie nights or catching up on your favorite shows. The adjacent dining area and fully equipped gourmet kitchen provide both style and convenience, whether you're preparing a quick breakfast or hosting a family dinner.brThe main living area also opens up to a screened-in deck with a dining table, perfect for enjoying a meal or drinks while staying cool in the shade. With the gentle Siesta Key breezes flowing through, this space adds another layer of comfort to your experience.brbrRestful Bedrooms with Private Balconies for Ultimate RelaxationbrCasa Leone comfortably accommodates up to 10 guests with 4 beautifully appointed bedrooms and 3 full baths. The main bedroom suite features a king-sized bed and its own ensuite bathroom with a stand-up shower, ensuring privacy and comfort. Step outside from the master to your own private balcony, where you can relax and enjoy the serene surroundings. The other three bedrooms, including a cozy bunk room for the kids, ensure everyone has their own space to unwind. Luxurious linens are provided in each bedroom, adding a touch of indulgence to your stay.brbrPrivate Outdoor Oasis: Pool, Spa, & Putting GreenbrStep outside into your own private paradise. The heated pool and spa offer a luxurious way to cool off and relax, while the private putting green provides a fun activity for guests of all ages. Whether you're lounging by the pool, dining al fresco in the screened-in deck area, or enjoying a friendly round of golf, this outdoor space is the perfect complement to the Siesta Key lifestyle.brbrPerfect Location Just minutes Siesta Key's BestbrCasa Leone is ideally located offering a tranquil escape with stunning water views. The world-renowned Siesta Key Beach is just 3 miles away, and the vibrant Siesta Key Village, with its eclectic mix of dining, shopping, and entertainment, is right at your fingertips.brbrWhy Wait Book Your Dream Vacation at Casa Leone Today!brWith its luxurious amenities, prime location, and seamless blend of indoor and outdoor living, Casa Leone is the perfect destination for a Siesta Key beach getaway. Whether you're relaxing by the pool, exploring the island, or enjoying quality time with loved ones, this home promises an unforgettable experience. Book your stay today and let Casa Leone be the backdrop for your perfect beach vacation!brbrCasa Leone can accommodate up to 10 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1) - Sleeps: 2br• Bedroom # 2: Queen Bed (1) - Sleeps: 2br• Bedroom # 3: Queen Bed (1) - Sleeps: 2 + Bunk Bed - Twin Bed (2) - Sleeps: 2br• Bedroom # 4: Queen Bed (1) - Sleeps: 2brbrWe 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 property is registered as a vacation rental with the City of Sarasota with a Registration Number of VR22-00008. Due to City of Sarasota vacation rental code, this property must be rented once during a seven (7) day period and have a maximum occupancy of 10 guests. This pool is heated from November 15th to April 15th.

Pet Friendly Home on Siesta Key w/ Private Heated Pool & Putting Green

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$297.2

Bayside Endless Summer | Walk to Siesta Key Beach, Community Pool, & Tennis Courtbrbr Why You'll Love This HomebrJust a short walk to the world-renowned Siesta Key Beach, Bayside Endless Summer offers a contemporary island retreat within the amenity rich Gulf & Bay Bayside community. Start your mornings on the screened lanai, then head out for a beach walk or a relaxing dip in the community pool. Spend your afternoons exploring Siesta Key Village, or staying active on the community tennis and pickleball courts.brbr⭐️ Perfect ForbrFamilies, couples, and smaller groups seeking close beach access, and a comfortable home base near Siesta Key's loved attractions.brbr☀️ Imagine ThisbrWake and get started in the open kitchen and dining space. Flip some pancakes or eggs in the well stocked kitchen. After breakfast, grab the provided beach gear and head just 0.6 miles to Siesta Key Beach, where powdery sand and clear teal waters set the tone for a perfect day.brbrIn the afternoon, return home to relax in the comfortable living space or on the furnished lanai. If you're feeling energized, take some laps in the community pool or play a match on the tennis courts. Later, head to South Siesta Key Village to explore shops, live music, and a variety of dining options from Captain Curt's to Lenny's Island Grill. As night falls, retreat to the primary suite and expansive bathroom, settle into soft linens, and end the night knowing another beach day awaits.brbr ️ Where You'll Sleep br• Bedroom 1: King Bed, Ensuite Bath with Walk-In Shower, TVbr• Bedroom 2: Two Full Beds, Hall Bath with Walk-In Shower, TVbrbr ️ Explore The Areabr• 0.6 Miles (13-Minute Walk) to Siesta Key Beachbr• 1.0 Miles to Crescent Beachbr• 1.3 Miles to Captain Curt's Crab & Oyster Barbr• 1.7 Miles to Siesta Key Village - Dining, Shopping, and Nightlifebr• 11.5 Miles to Sarasota-Bradenton International Airport (SRQ)brbrDon't Wait: This neighborhood is in an incredible location on Siesta Key and provides tranquility and privacy. Book your dream stay today. Your reservation includes peace of mind with our CottageClean™ program, featuring a six-hour deep clean and a 35-point inspection before every stay—ensuring your home feels fresh, safe, and truly vacation-ready upon arrival.brbrNeed To Know: This condo is located in the Gulf & Bay Bayside community. This allows guests staying at this unit to utilize the included community amenities. The community pool is seasonally heated. Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights. Free high-speed WiFi is included.

Bayside Endless Summer | Walk to Siesta Key Beach, Community Pool, & Tennis Court

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$511.84

This must-see, beautiful home on Siesta Key offers a much sought after modern and contemporary design. This unit, located on the 2nd floor above the garage, has 3-bedroom, 2.5-bathrooms and can sleep up to 6 guests. Enjoy the fresh island breeze from your balcony, or step outside and relax in the warm sun by the pool, private to the Ocean Vue units. Less than 300 feet from beach access #11, this home offers quick access to the #1 rated Siesta Beach! You can even take the short walk into the Siesta Key Village where you can experience the many great shops, restaurants, and live entertainment the island has to offer. br*This property is stairs only; all guest must have the ability to climb stairs.br*No garage parking. Driveway parking only.brbrBedroom 1: KingbrBedroom 2: QueenbrBedroom 3: 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 Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 27br*Security Authorization Hold taken upon check-in. Amount: $1,500

Stunning 3 Bedroom / 2.5 Bath Condo Steps from Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$634.62

Siesta Dolce | Private Pool, Kayaks and Putting Greenbrbr Why You'll Love This HomebrEscape to Siesta Dolce, a luxurious oasis where every detail is designed for your ultimate enjoyment. From its stunning outdoor amenities, including kayaks and a putting green, to its inviting interiors, this home promises an unforgettable Siesta Key escape.brbr ‍ ‍ Perfect ForbrFamilies or adult groups seeking a blend of active outdoor fun and luxurious relaxation, with easy access to Siesta Key's acclaimed beach and village.brbr ️ Imagine ThisbrYour morning begins with a serene paddle in one of the kayaks along the peaceful canal, greeting the sun. Back at the villa, challenge your companions to a friendly game on the 3-hole putting green before a refreshing dip in the private heated pool, then lounge on one of the four poolside lounge chairs. Lunch is served al fresco at the poolside dining table with an umbrella, followed by an afternoon unwinding in the outdoor rattan hanging basket chairs or swaying gently in the hammock. As evening approaches, gather around the fire pit for s'mores and stories, or sink into the plush outdoor L sectional for cocktails under the stars. Inside, the sunken den offers a cozy retreat, while the fireplace in the living room provides a warm ambiance on cooler evenings. Dinner is a joy to prepare in the well-appointed kitchen, featuring a distinctive French sink. Later, unwind with a good book, reflecting on another perfect day in paradise.brbr Where You'll SleepbrBedroom 1: King Bed (Remote Adjustable), Ensuite BathbrBedroom 2: King Bed (Remote Adjustable), Ensuite BathbrBedroom 3: King Bed, Shared BathbrBedroom 4: Two Twin Beds, Shared Bathbrbr Explore the Areabr• 1.5 Miles to Siesta Key Beach – Quick Walk to Sand and Gulf Watersbr• 1.8 Miles to Siesta Key Village – Dining, Shops, and Entertainmentbr• 4.3 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Restaurantsbr• 3.7 Miles to Crescent Beach – Shelling, Snorkeling, Sunbathing brbr ️ Your Siesta Key Adventure AwaitsbrDon't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspectionbrbrNeed to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. This property is registered as a vacation rental with the City of Sarasota with Registration Number VR23-00018. Due to City of Sarasota vacation rental code, this property must be rented once during a seven (7) day period and has a maximum occupancy of 8 guests. We happily welcome up to 2 small dogs (up to 25 lbs) with a $250 fee per pet, breed guidelines apply to ensure a safe and comfortable stay for everyone. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather.

Siesta Dolce | Private Pool, Kayaks and Putting Green

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$297.27

Welcome to Our House at the Beach C-110 by Tropical Sands Accommodationsbr1113 Lake House Cir #110 Siesta Key, FL 34242brbrbrExperience island comfort and unbeatable convenience at Our House at the Beach C-110, a beautifully appointed two-bedroom, two-bath townhouse located just across the street from world-renowned Siesta Beach, the only lifeguard-protected beach on Siesta Key. This Lake House suite offers easy access to everything you need for a relaxed and memorable Gulf Coast getaway.brbrHighlights:br• A Heated Swimming Poolbr• 4-Minute Walk to the Beachbr• 2-Minute Walk to trolley Stopbr• Two Tennis Courts and a Pickleball Court for Active Funbr• A Gas grilling Pavilion and Picnic Areas Under Shaded Treesbr• Beach Chairs and a Beach Cart brbrWelcome to your freshly updated beach townhouse, where coastal elegance meets comfort. The bright and airy living room features beautiful wooden floors, a large flat-screen TV, and a cozy sectional, perfect for relaxing after a day in the sun. The sliding glass doors open to a private patio with outdoor seating, ideal for sipping your morning coffee or unwinding in the ocean breeze. The modern kitchen is fully stocked with stainless-steel appliances, including a refrigerator, stove, oven, and dishwasher, along with a microwave, toaster, and drip coffeemaker. Whether you're preparing a full meal or a quick snack, this beachside vacation rental has everything you need for a stress-free stay on the Gulf Coast.brbrThe primary bedroom features a plush king-size bed and a private ensuite bathroom. The second bedroom offers a cozy queen bed with access to a full hallway bath. Two rollaway beds provide flexible sleeping arrangements for families or small groups. Enjoy the added convenience of an in-unit washer and dryer, Wi-Fi throughout, and two dedicated parking spots, one in a private garage and one guest space.brbrRoom Details brbr-Primary Bedroom: King bed and ensuite bathroom with a walk-in shower br-Second Bedroom: Queen bed br-Bonus: Two Rollaway BedsbrbrWhether you're planning a weeklong retreat or a seasonal stay, Our House at the Beach C-110 delivers the perfect blend of comfort, convenience, and classic Siesta Key charm.brbrReserve your dates today and get ready for sun, sand, and relaxation in one of Florida’s top rated beach destinations!brbr-brbrThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis property does not allow pets of any kind.

Our House at the Beach C-110: Across the street from the beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$375.73

Enjoy this comfortable, 3rd floor, garden view condo. Wifi internet available for your use. Comfortably sleeps 4 people. Recently updated living area and kitchen which included: Entire kitchen - all new cabinets, ceramic flooring, lighting, granite counter tops, back splash and new black appliances; Newly painted kitchen, living room, dining room and extended lanai; Ceramic flooring in the kitchen, living area and dining room; 6 Panel solid hardwood doors, California type shutters or bifold-pine door (master bedroom); Continuous extended lanai with white tropical fan and light for reading (on a remote control). Full hurricane sliding tinted glass doors with continuous pull roller shades for shade and/or openness; Bedrooms have hurricane tinted glass.

Updated, 3rd Floor Garden Condo with a View!

Siesta Key, Florida, United States

1

Bed

Bath

4

Sleeps

$326.73

We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium/community in one convenient location.brbrAs you enter the condo, your eye is immediately drawn to the bright and cheery living space and wall ...of sliding glass doors that open up to the balcony. Southern exposurebathes the condo in sunshine through large sliding glass doors in each room. The sliding gass doors open to create an indoor/outdoor living space where you can relax with picturesque views of the Intercoastal Waterway and the Gulf of Mexico. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: Yesbrbr- Beach Access: Privatebrbr- Bed Size 1st/Master: Kingbrbr- Bed Size 2nd Rm: 2 Twinsbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 6th Floorbrbr- Internet Access: Yes, Privatebrbr- Walk in shower: Yesbrbr- Parking: Yesbrbr- Parking Space Type: 88brbr- Electric Stove: Yesbrbr- View: Canalbrbr- PICKLEBALL: Yesbrbr- Bay View: Yesbrbr- Gulf View: PARTIALbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 607

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$466.64

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 3 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.br* Anchorage Resort Condobr* 3 bedrooms / 2 bathroomsbr* Sleeps up to 8br* Spacious Balcony overlooking Northern Siesta Keybr* Third Floor Condo above the treetopsbr* Fully equipped Kitchen with seating for 6 at the dining tablebr* Beach Supplies include- Chairs, Umbrella, Cooler, Raft/Float Items, Beach Towelsbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Second Floor Condo)brBedroom 1: One King Bed (Attached Bathroom) 50 TVbrBedroom 2: Two Doubles Beds 19 TVbrBedroom 3: One Queen Bed 24 TVbrbrPool Information:br- Community Poolbr- HeatedbrbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbr brThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each Floorbr brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 3 Bedroom/3rd Floor Condo with Balcony

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$215.8

Our condo is located in the heart of Siesta Key Village which has numerous restaurants, bars, shops and a grocery store and is only 1 block from the beach! The best of both worlds as everything you need is within walking distance.brbrProperty Description - In the main room you have a queen size murphy bed with a built in couch that folds under the bed. With our small space we needed things that could function in multiple roles and will be out of the way when not in use. On either side of the murphy we have lined the wall with drawers, shelves and hanger space for your stay. Opposite the murphy bed is a modular couch and coffee table. A wall mounted 40 LED LCD TV with YouTubeTV HD service is mounted on an articulating arm and will allow you to watch while seated in the couch or while lying in bed. For temperature control we have a Daikin ductless AC/heat pump with a convenient hand-held remote control with precise temperature control. brbrIn the kitchen, there's a GE Speed cook oven which is so much more than just a microwave. You can convect, speedcook, microwave and warm/broil. The 2 drawer fridge and freezer tuck under the quartz countertop and next to that is the combo ventless washer/dryer. Plenty of dishes, cups, pots, pans and a 3 place burner for any sized meal. This unit does not have a dishwasher.brbrIn the bathroom we have a full tile shower with a hand-held shower head. A new vanity and cabinet plus a shelf over the shower offer plenty of storage.brbrOutside we have a patio with chairs, table and umbrella to enjoy a meal or company. Cook your meal in the small charcoal grill that is provided as well. There is an outside shower and hose to spray down after your swim in the ocean and a beach cart along with chairs and other beach essentials for you to use during your stay.brbrLocation - Our property is located directly within Siesta Village on the beach side which means you are close to the restaurants and bars yet away from all the traffic on Ocean Blvd. In addition, I feel that we have the best beach on Siesta as we are located South of Big Pass and all of the marine traffic passes directly in front of you while you relax on the beach. Manatees (in the summer), dolphins, tarpon, you will see it all here and you see it in an abundance found no where else on the Gulf side of Siesta.

Steps from Siesta Village and the Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$363.94

HIDE-A-WAY Suite - A Charming, Newly Refurbished RetreatbrbrWelcome to the enchanting Hide-A-Way Suite, a beautifully updated 1-bedroom, 1-bath ground-floor apartment offering 580 sq.ft. of comfort and style. brbrNestled in a serene, non-smoking environment, this suite comfortably accommodates up to 4 guests with a king-size bed and a luxury queen self-inflating air mattress in the living room. brA charming round table with two elegant chairs creates the perfect nook for dining, morning coffee, or intimate conversations. brThe table’s smooth, polished surface invites you to relax and enjoy a cozy meal, while the comfortable chairs, designed with soft cushions and a modern yet timeless look, add both style and comfort to your space.brbrAll bedding is hypoallergenic, ensuring a restful sleep for all.brbrFrench doors open to a sunny patio deck, where you can enjoy a romantic breakfast or unwind with a book, all while overlooking the stunning black-bottom heated waterfall pool. brbrThe fully equipped kitchen is perfect for meal prep and includes a washer/dryer for added convenience. Both the living room and bedroom feature flat-screen TVs with YouTube for your entertainment.brbrFor your comfort, the suite is fully air-conditioned and heated. Complimentary amenities include on-site parking (1 car), beach chairs, sun umbrellas, 5G Wi-Fi, and family-friendly items like a pack & play and a high chair.brbrPlease note, this unit does not allow pets, and we exclusively rent from Saturday to Saturday during high season (February - April). brbrTo ensure smooth communication, please provide your email and cell phone number when booking so we can send you essential arrival and departure instructions.brbrWe look forward to welcoming you to this relaxing coastal retreat!br— Virginiabr

Apartment

Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$428.18

Aloha Kai #28brbrA Siesta Key Beachside Bliss Awaits!brbrEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #28. This charming beach 2-bedroom house is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Crafting abundant serenity in a snug design, Aloha Kai #28 invites you to kick off your shoes, have a grill on your back patio, and dive into a world of relaxation and adventure. Here's what makes this home so special:brbrBedding Arrangement:br2 Bedrooms:brMaster Bedroom with Queen-size bed, Smart TV and Ensuite BathroombrGuest Bedroom 1 with Two Twin-size beds, and Smart TVbrAdditional Sleep: 1 Sleep Sofa in the Living AreabrTop Features:brSleeps 6brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort.brBack Patio: Enjoy balmy evenings at home on the back patio to relax and unwind after an eventful day.brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun.brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #28 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this little gem offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #28 today and create memories that will last a lifetime!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.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass

Beach Life! it Doesn't Get Any Better than This! - Aloha Kai #28 - roelens

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$271.62

Aloha Kai #18brbrA Siesta Key Beachside Bliss Awaits! br brEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #18. This charming beach studio is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Packing ample charm into a compact space, Aloha Kai #18 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special: br brBedding Arrangement: brStudiobrCommon Area with King-size bed and Smart TV brTop Features: brSleeps 2 brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation. brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort. brFront Screened Porch and Back Patio: Sip coffee in the mornings in your screened porch or curl up with a good book. Enjoy balmy evenings at home on the back patio to relax and unwind after an eventful day.brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun. brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #18 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this little gem offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #18 today and create memories that will last a lifetime! 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: br**10% 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.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass

Charming Beachside Retreat - Aloha Kai #18 - Roelens

Siesta Key, Florida, United States

1

Bed

1

Bath

Sleeps

$303.07

One of Our Most Beautiful Condos on Siesta Key – Luxury 2BR/2BA Gulf-Front EscapebrbrWelcome to one of our most beautiful and professionally decorated condominiums on Siesta Key. This stunning two-bedroom, two-bath residence offers over 1,200 square feet of beautifully upgraded living space and showcases the very best of coastal luxury.brbrDesigned with elegance and comfort in mind, this immaculate condo features high-end finishes, designer furnishings, and thoughtful upgrades throughout. From the moment you enter, you’ll be impressed by the light-filled open layout, refined décor, and resort-style ambiance.brbrThe spacious living area opens to a private screened lanai—perfect for enjoying Gulf breezes, morning coffee, and breathtaking sunsets. The fully equipped kitchen features modern appliances, quality cabinetry, and everything needed for preparing meals at home.brbrThe primary suite is a true retreat, offering a king bed, serene coastal décor, and a beautifully updated en-suite bathroom. The guest bedroom features two twin beds, making it ideal for children, friends, or additional guests, with convenient access to the second full bath.brbrAdditional features include high-speed wireless internet, flat-screen TVs and premium furnishings throughout.brbrLocated just steps from the world-famous white quartz sands of Siesta Key Beach, this exceptional condo places you in the heart of paradise. Guests enjoy resort-style amenities including a heated Gulf-front pool, fitness center, BBQ grilling area, BBQ grilling area, and beautifully maintained tropical grounds. Restaurants, boutique shopping, and the free village trolley are all nearby for easy exploring.brbrWhether you’re planning a relaxing beachfront escape or a memorable family vacation, this immaculate condo delivers luxury, comfort, and unforgettable coastal living.brbrBook early—this is one of our most sought-after and beautiful residences.

One of our Most Beautiful Condos on Siesta Key Luxury 2BR/2BA Full Gulf Views

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$501.73

Welcome to Surfside! Where you will experience beautiful Siesta Key Living! This 3-Bedroom, 2.5-bathroom home sleeps up to 6. Relax on the spacious rooftop sun deck and take in the amazing sweeping views of our world-famous beach, Siesta Key. Inside, on the first living level, you will find a large, open living area, a half bathroom, a nice sized balcony for enjoying that island breeze, and a large kitchen with plenty of space to cook in. The second living level has 3 bedrooms, 2 full baths, a washer and dryer, and another balcony off the bedrooms. Up one more flight of stairs is the large rooftop sun deck, perfect for watching gorgeous sunsets all year round. This home is equipped with 2 parking spaces: 1 in the drive way and 1 carport space in the rear. For your convenience, there is an onsite beach access path that will lead you to the sugary sands and crystal-clear waters. This home is just a short stroll to the Siesta Key Village with a large variety of dining and shopping options. Capture your piece of paradise with this fabulous Siesta Key townhome.br*Stairs only. All guests must have the ability to use stairs.brbrBedroom 1- KingbrBedroom 2- QueenbrBedroom 3- 2 Twin Bunk BedsbrbrAdded 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 Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 27br*Security Authorization Hold taken upon check-in. Amount: $1,000

Spacious 3 Bedroom Gulf Side Townhome with Rooftop Sun Deck On Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$283.4

Welcome to the beach lover's paradise, Condo 409! This little treasure trove offers you front-row seats to the Gulf of Mexico's breathtaking views from the Siesta Key Beach. With over 820 sq. ft of living space, this 1-bedroom and 1-bath condo flaunt a king-sized bed, a queen-sized sleeper sofa, and a kitchen fitted with all the necessary equipment for your cooking and entertainment needs. The cherry on top Two flat-screen TVs to keep you company!brbrBut wait, it gets better! Sip your morning coffee while gazing at the mesmerizing views of the Gulf from your very own screened-in lanai. Siesta Key sunsets are a sight to behold, and you'll be left speechless with the colors of the sunset bouncing off the white quartz sand of Siesta Key Beach.brbrAnd of course, you're just a hop, skip, and a jump away from the beach, with our beach kit loaded with chairs, towels, and an umbrella. Once you've had your fill of the beach, take a dip in the heated pool or work on that beach bod in our gym. Need more options The Village is just a short walk or free trolley ride away, and you'll find yourself spoilt with dining, shopping, and nightlife options.brOur onsite management team is always here to make your stay extra special, so book your stay today and experience the ultimate beach getaway in Condo 409!

Prestine 1 Bed 1 Bath at Siesta Key Beach with Gulf Views Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$298.21

Experience the ultimate Siesta Key vacation with the picturesque unit 515 at Crescent Royale. This spacious 2-bedroom and 2-bathroom condo offers a serene ambience with stunning views of sunrise and sunset from the screened lanai. The unit features traditional Florida decor and comes fully equipped with all the modern amenities to provide you with a comfortable and memorable stay.brbrThe primary bedroom boasts 2 queen-sized beds, while the guest room is furnished with 2 twin beds, making it perfect for families or groups of friends. The unit also includes beach chairs, umbrellas, and towels, ensuring you have everything you need to enjoy a fun day at the world-renowned Siesta Key Beach. brbrWhen you're ready for a change of pace, Crescent Royale provides access to a heated pool, workout facility, shuffleboard court, and BBQ area.brbrNo trip to Siesta Key is complete without a visit to Siesta Key Village, which is easily accessible by a free trolley or short stroll away. The Village offers an array of dining options, souvenir shops, nightlife, and fantastic people-watching. Additionally, unit 515 offers some of the best on-site views available.brbrBook your stay at unit 515 today, and discover why Siesta Key stands out as America's favorite destination.

Siesta Key Sunsets 2 Bed 2 Bath Top Floor With Gulf Views Steps To Beach

Siesta Key, Florida, United States

Bed

Bath

5

Sleeps

$352.03

Indulge in a perfect beach vacation at Condo 511, offering stunning views of The Gulf and Siesta Key Beach from the fourth floor. This 1220 square foot condo features 2 bedrooms, 2 full bath rooms and has a relaxing and casual beachy vibe, inviting you to unwind and enjoy America's top-rated beach.brbrThe condo comprises two bedrooms and two full bathrooms, with the master bedroom featuring a king-sized bed and the guest bedroom offering a queen-sized bed. Moreover, the kitchen is fully equipped with everything necessary to prepare delicious meals.brbrFor your entertainment, the condo is equipped with four flat-screen TVs, basic cable, and free wifi. Step out of the condo, and you are only a few steps away from Siesta Key, the most admired beach in America, renowned for its white quartz sands and crystal-clear waters. You can also enjoy the world-renowned sunsets from the screened-in lanai. With some of the most picturesque views on the key, you are guaranteed to have a memorable vacation.brbrLocated in the heart of Siesta Key, you can take a free trolley ride or a short stroll to Siesta Key Village, where an endless array of restaurants, nightlife, and souvenir shops await you. Crescent Royale, the condo's location, offers a heated pool, workout gym, BBQ area, and shuffleboard court to keep you entertained throughout your stay. The on-site management team is always available to ensure your vacation runs smoothly.

Siesta Key Gulf Panoramic Views 2 Bed 2 Bath Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

5

Sleeps

$334.07

Welcome to Condo 312, the epitome of luxury beachfront living. This gold-rated condo boasts an array of amenities to ensure you have a memorable vacation. With two bedrooms, two baths, and an expansive 1,220 square feet of living space, its beauty is simply breathtaking. Notably, it's situated right next to the best beach in the US, giving you a full, panoramic sea view from your screened-in lanai!brbrThe master bedroom is fit for royalty, featuring a king-sized bed, while the second bedroom has a twin and double bed, ideal for families or friends. Additionally, there's a sleeper sofa to cater to extra guests. The kitchen is well-equipped with modern amenities, including a kitchen island, making cooking a breeze.brbrPacking for a beach vacation can be tedious, but fret not! We've got you covered with towels, linens, beach chairs, and umbrellas all provided in the condo. All you need is to pack your swimsuit, sunscreen, and flip flops, and you're good to go!brbrAfter a full day at the beach, picture yourself enjoying world-renowned sunsets with a glass of wine from the screened-in lanai. Alternatively, take a free trolley ride to the Village, where you can indulge in an array of dining, nightlife, and shopping options.brbrCrescent Royale's beach-facing suites and heated pool are perfect for a refreshing dip or a BBQ party. Fitness enthusiasts can take advantage of the onsite workout gym. With our dedicated onsite management team, your vacation is guaranteed to be stress-free.brbrThis condo has everything you need for your dream beach vacation. All that's missing is YOU! Make your dream a reality and book now!

Siesta Key Beach Gem 2 Bed 2 Bath with Full Gulf Views Steps to Beach

Siesta Key, Florida, United States

Bed