Vacation Rentals By Owner In Siesta Key, FL

Amazing Condo to stay with family and friends close to every single attraction in Siesta Key FL, Close to beaches and restaurants offering two full bedrooms with two full baths with full Bay views from your wrap around Balcony. Deeded Beach access steps away. 2 month minimum stay. Amazing pool and Jacuzzi with Barbecue Grills included.

Amazing Condo in Siesta Key Florida.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$313.12

Gulf and Bay Club Unit F407 by Tropical Sands Accommodations brbrExperience the beach life at Gulf and Bay Club Unit F407! This updated Siesta Key condo features two bedrooms and two bathrooms, making it perfect for families and friends seeking a rejuvenating getaway. You’ll enjoy exclusive access to a private beach area with secured entry and a short walk to Siesta Key Village shopping and dining. brbrHighlights br• Private Beach with Secured Access br• 3 Shared Heated Pools br• Shared Tennis, Pickleball, Racquetball, Basketball, and Shuffleboard courts br• Shared Fitness Center br• Community Electric Vehicle Chargers br• 1 assigned Covered Parking Spot br• Shared BBQ areas br brGulf and Bay is a fabulous beachfront condominium complex with private beach access to Siesta Key Beach and its world-famous white sands and warm waters. This complex features three heated pools, saunas, a hot tub, activity courts for tennis, pickleball, racquetball, and shuffleboard, a fitness center, and numerous tiki-themed BBQ areas surrounding the facility lakes. br brInside the condo, unwind in the spacious living room featuring a large sectional sofa and breathtaking beach views—the perfect setting for relaxation and memorable gatherings. The fully equipped kitchen dazzles with stunning cabinets and stainless steel appliances, ideal for preparing delectable meals. Both bedrooms are well-appointed with king beds, TVs, and luxurious bedding for a restful night's sleep. br brDon't wait! Book your stay at Gulf and Bay Club Unit F407 today and dive into the extraordinary Siesta Key vacation experience you've always dreamed of!

Discover Gulf and Bay Club Unit F407 in Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$242.47

Harbor Towers Unit 525 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers Unit 525, a spacious two-bedroom, two-bathroom condo in one of Siesta Key’s most desirable gated waterfront communities. Ideal for extended stays with a 13-night minimum requirement, this inviting retreat offers tropical garden views, comfortable living spaces, and access to resort style amenities just minutes from Siesta Key Beach and Siesta Key Village.brbrHighlightsbr• 2 Bedroom / 2 Bathroom condobr• King, 2 Queen bedsbr• 13-night minimum stay communitybr• Private balcony with tropical garden viewsbr• Short drive to Siesta Key Beachbr• Gated waterfront communitybr• 2 heated community poolsbr• 3 Har-Tru tennis courtsbr• 40-slip marinabr• Fitness center and saunabrbrHarbor Towers is known for offering amenities rarely found in many Siesta Key associations. Guests enjoy access to two heated pools surrounded by lush tropical landscaping, three tennis courts, and a 40-slip marina with direct access to the Intracoastal Waterway. The gated community also features a fitness center and sauna, making it especially appealing for snowbirds and extended stay guests seeking both relaxation and recreation.brbrUnit 525’s private balcony is a standout feature, offering peaceful views of swaying palms and manicured grounds. It is the perfect setting for morning coffee or unwinding in the evening breeze. The open living area features comfortable seating, a built-in entertainment center, and large sliding glass doors that bring in natural light and connect seamlessly to the balcony. The adjacent dining area provides a welcoming space for shared meals. The fully equipped kitchen includes warm wood cabinetry, granite countertops, and full-size appliances, making it easy to prepare everything from quick breakfasts to family dinners during your extended stay.brbrThe primary bedroom features a king bed, ample storage space, and a private ensuite bathroom with a shower and tub combination. The second bedroom is generously sized with two queen beds, making it ideal for families or guests traveling together. A hallway bathroom with a shower and tub combination is easily accessible from the guest bedroom and main living area. Each bedroom is designed to provide a comfortable and restful environment after a day exploring Siesta Key.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with shower and tub combinationbr• Second Bedroom: Two queen bedsbr• Hallway Bathroom: Shower and tub combinationbrbrHarbor Towers Unit 525 includes elevator access, assigned parking, community grilling areas, and beautifully maintained grounds. The 13-night minimum stay requirement creates a quieter, more residential atmosphere, perfect for seasonal visitors, families, and remote workers.brbrIf you are looking for a Siesta Key vacation rental with resort-style amenities, tropical views, and the comfort of an extended stay community, Harbor Towers Unit 525 by Tropical Sands Accommodations is the perfect choice. Reserve your preferred dates today and enjoy the relaxed coastal lifestyle that makes Siesta Key a favorite year after year.

Harbor Towers 525 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$245.86

Classic Mid-Century 2 bedroom, 2 bath home, believed to be designed by Sarasota School of Architect Ralph Twitchell or a close follower. It is located directly on Siesta Key’s Grand Canal and is nestled into a quiet, luxury neighbourhood. brbrWe tried to preserve the “Old Florida” bungalow vibe that is steadily disappearing. Decorated with furniture of the era, alongside modern elements from European designers. Sunlight floods into the panoramic windows from both sides of the house. Relax while enjoying the subtropical garden in front or the waterway out back. Dock your boat, drop a fishing line or go kayaking when the mood strikes. It’s a five minute bike ride to the top-rated Siesta beach or into the village. brbrThe entire house, garden, dock, shed and carports are available for guests to use during the stay. This house is best suited for a couple or small family. If you are looking to accommodate two couples, please note the wall between the two bedrooms is not fully soundproof, nor are the bedroom doors so it will be cozy. brbrAs soon as you arrive, kick up your feet and enjoy this wonderful Mid-Century bungalow. The location, and home itself will make you want to stay forever.

Mid-Century Meets Boaters’ Dream

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$392.96

Entirely Renovated, 2 Bedroom, 2 Bathroom Garden View Unit in the Beachfront Property of Siesta Dunes. This unit features a brand-new Kitchen with new white cabinets, stainless steel appliances, granite countertops and a refinished ceiling with canned lighting. The Master Bedroom has 2 new queen beds. The master bathroom area has new cabinets, granite counters, fixtures and new lighting. The master bathroom has a shower. The Guest Bedroom has 1 new king bed. The Guest Bathroom was completed renovated and includes a new shower, all new cabinets, lighting and fixtures. The living area has all new furniture including a new couch, tables and a new wall mounted Television. This unit will not disappoint!

Renovated 2 Bed/2 Bath Garden View Unit in Gulf Side Property

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$617.75

At Sun Sea Terrace | Rooftop Views + Steps to Siesta Beach & Villagebrbr Why You'll Love This HomebrStart your morning with panoramic rooftop views, then stroll just 0.2 miles to the powder-soft sands of world-famous Siesta Key Beach. Nestled above Siesta Key Village, At Sun Sea Terrace is a rare penthouse escape with six private balconies, a rooftop terrace, and seamless indoor-outdoor flow for laid-back luxury living.brbr ‍ ‍ Perfect ForbrIdeal for families, couples, or friend groups seeking elevated comfort, walkability, and that “never-want-to-leave” vibe just moments from the Gulf.brbr ️ Imagine ThisbrBegin your day on the rooftop terrace as sea breezes drift across the Village skyline. Head down for a morning walk on the beach—just 0.2 miles away—then grab brunch steps from your front door. Back at home, unwind in the media room with a cool drink from the bar, or catch up on work from your private office nook. Evenings are made for alfresco dinners under the stars, followed by a soak in the shared heated spa. With six balconies to choose from, sunset views and stargazing await every night.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath br• Bedroom 2: King Bed, Ensuite Bathbr• Bedroom 3: Queen Bed, Shared Full Bathbr• Bedroom 4: King Bed, Shared Full Bathbrbr Explore the Areabr• 0.2 miles to Siesta Key Beachbr• 0.1 miles to Siesta Key Villagebr• 0.3 miles to Sun Garden Cafébr• 0.4 miles to Beach Bazaar of Sarasotabr• Kayaking, Paddle Boarding, and Parasailing Nearbybrbr⌛ Don't WaitbrHomes like At Sun Sea Terrace book fast. Your stay includes our CottageClean™ Program, featuring a six-hour deep clean and 35-point inspection for peace of mind and pristine comfort from the moment you arrive.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. This home is part of a condo 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, 3rd, and 4th floors of the building, the left most garage, along with the shared outdoor and pool areas. Contact us directly for more information regarding any shared space for this vacation home. This home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.brbrPer HOA requirements:br• Garages can fit a vehicle no bigger than 72 inches in height.br• Guest vehicle height will be needed before arrival as to prevent any missed expectations or negative effects to your experience.br• One parking pad per side of the building can be used as a first come, first serve basis.br• Oversized or extra vehicles to be parked on the street just outside the gates of the property.br• Grills may only be used on ground level, pulled 10 feet from the building. No grills, hibachi, or any open flame cooking device or fire pit may be used on balconies or patios.

At Sun Sea Terrace | Luxury Siesta Key Condo w/ Heated Pool, Short Walk to Beach and Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$690.96

Escape to Siesta Key's Hidden Treasure – A Peaceful, Private Island RetreatbrbrWelcome to Siesta Key's Hidden Treasure, a delightful, tranquil escape offering the perfect balance of comfort and luxury. This charming property features a spacious 2-bedroom, 2-bathroom main house and a detached 2-bedroom, 1-bathroom Casita, ideal for larger groups or families looking for both shared and private spaces. Whether you're seeking relaxation or adventure, Hidden Treasure has everything you need for an unforgettable getaway.brbrCharming and Comfortable Living SpacesbrStep inside the main house, where you'll find a bright and cheerful atmosphere designed to make you feel right at home. The main bedroom serves as a peaceful retreat, complete with a luxurious ensuite bath featuring double sinks, an opulent shower, and a seated dressing vanity. The detached Casita off the screened patio provides a cozy, private getaway with a king bedroom, a twin bedroom with two beds, and a shared full bath. With 2 king beds, 1 queen bed, and 2 twin beds, the home comfortably accommodates up to 8 guests, perfect for families or friends. Fresh linens are provided for your convenience.brbrOutdoor Paradise AwaitsbrThe heart of this home lies in the screened pool and patio area, a true backyard oasis. Step through the sliding glass doors into a tropical paradise, featuring a private heated saltwater pool, a hot tub, multiple dining areas, and an elevated sun deck perfect for soaking up the sun. Relax poolside in the spacious courtyard, fire up the grill, or enjoy a meal while basking in the gorgeous island weather. As the day winds down, gather around the fire table for breathtaking sunset views. The Banyan tree with its sprawling roots stands as the centerpiece of the lush, tropical landscape, offering an enchanting atmosphere.brbrFully Equipped for a Seamless StaybrThe home provides all the essentials to ensure a stress-free vacation. Brew your favorite coffee using the regular or Keurig coffee maker, prepare meals with the fully equipped kitchen, and enjoy the convenience of a dishwasher, washer/dryer, and other amenities for a hassle-free stay.brbrIdeal Location for Siesta Key AdventurebrHidden Treasure offers the perfect location for enjoying all that Siesta Key has to offer. In just minutes, you can sink your toes into the powdery white sands of Siesta Key Beach, renowned for its beauty and serenity. Take a scenic stroll or bike ride to the charming Siesta Key Village, where you'll find a variety of dining, shopping, and entertainment options.brbrBook Your Escape TodaybrWhether you're lounging by the pool, exploring the nearby beach, or simply enjoying quality time with loved ones, Hidden Treasure is the perfect place to create lasting memories. Book your stay today and experience the ultimate Siesta Key getaway, where relaxation, comfort, and natural beauty come together.brbrExclusive Amenities Include:br• Private Screened Saltwater Heated Poolbr• Private Hot Tubbr• 10 Minute Walk to Siesta Key Villagebr• 15 Minute Walk to Siesta Key Beachbr• 2 Bedroom Detached Private Guest Quartersbr• 4 Bedrooms, 3 Full Baths (1 Master Bedroom)br• 2 King Bed, 1 Queen Beds, 2 Twin Beds (Sleeps 8) with linens providedbr• Sun Deckbr• Outdoor Dining & Lounge areabr• Private Garagebr• 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• Beach Towels, Chairs, Cooler, & Caddy Providedbr• Free WiFi & 4 HDTV'sbr• Gas Grillbr• Enhanced cleaning protocols provided by our CottageClean Teambr• Island Shuttle Transportation AvailablebrbrHidden Treasure can accommodate up to 8 guest with a bedding configuration as follows:brbrMain Cottage:br• Bedroom # 1: King Bed (1) - Sleeps: 2br• Bedroom # 2: Queen Bed (1) - Sleeps: 2brbrPrivate Casita Guest Quarters:br• Bedroom # 3: King Bed (1) - Sleeps: 2br• Bedroom # 4: Twin Beds (2) - 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: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th.

Hidden Treasure | Located on Siesta Key w/ Private Heated Pool/Hot Tub & Spacious Outdoor Area

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$237.41

Welcome to Bay Oaks! Only minutes to Siesta Beach, restaurants and shopping. This cozy, 2nd floor, 2 bed, 2 bath unit with over 1,100 sf of living space comfortably sleeps 4. Large TVs in master and living room, comfy beds and furniture. Enjoy the lanai while overlooking the beautiful resort-style heated pool. Assigned parking right near unit. Walk to the pier to watch the boats cruise along the inter-coastal, play tennis, or simply relax. No matter what you chose, you will love it here!brbrOur ultimate vacation rental in a home that really has it all.brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrThis captivating 2-bedroom, 2 bathroom home features all the amenities you can think of for your beach vacation and offers an unbeatable location. This home is ideal for families, couples, and even singles.brbrThis home can accommodate up to 4 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1) br• Bedroom # 2: Twin Bed (2)brbrExclusive Amenities Include:brbr• Lanai overlooking heated poolbr• Fishing Pier and Dockbr• Washer/Dryerbr• Tennis Courtsbr• Clubhousebr• Dining Tablebr• Secure Covered assigned parking spacebr• Gourmet Kitchenbr• Free Hi-Speed WIFI br• Free assigned parkingbrbrApprox drive times to airport and major attraction cities:br5 to 15 min - beaches, theater, restaurants, shopping, and morebr20 min - SRQ Airportbr30 min - Outlet mallbr50 min - St Petebr60 min - TPA Airport/Port of Tampabr2hr - Disney WorldbrbrI live very close and am always available if you need something. I want your stay to be enjoyable so please contact me if you need assistance.brbr1/3 mile walk to Beach Access #12 or take the Free trolley that stops at the entrance every 30 minutes.brbr10 minute walk to Beach Access #12. brFree Trolley stops at entrance about every 30 minutes that travels up and down the key all day.brbrRental age restrictions:br-This property has a minimum primary renter age requirement of 25. br- Upon booking, a signed rental agreement and government issued photo identification are required prior to receiving an electronic access code to the property.br- This is a no-pet property.br*Due to online booking policies, some payments may need to be submitted after the booking is reserved and confirmed. Please let us know if you have questions about the policies prior to booking.

Apartment

Huge Heated Pool ❤ Short Walk to the Beach, ride FREE Trolley around the Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$163.85

Beautiful 4'th floor condo with elevator access. screened in lanai, all the essentials, and beach chairs, umbrellas, cooler with wheels and big beach bag and towels.bra one mile drive to Siesta key beach and a 10 minute walk to Crescent beach.brtennis court, fishing dock and BBQ area with picnic tables on the intercoastal waterway. Heated swimming pool, coin op laundry, and club house with pool table, lounge area and tourist info brochures.

Beautiful one bedroom condo on Siesta Key. minutes from Siesta key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$408.09

Experience the Gulf breeze and partial views with this lovely 2-bedrom, 1-bathroom home directly across from our world-famous Siesta Key Beach! Beautifully decorated, this home features a king bed in the master, a queen in the second bedroom, and a queen sleeper sofa in the living room, accommodating up to 6 guests. This unit, located on the second floor, is right outside of the Siesta Key Village, making it a breeze to walk to many of the restaurants, shops, and live entertainment the island has to offer. Relax in the sugary white sand or swim in the crystal-clear waters. Enjoy the brilliant colors of sunset at this beautiful vacation home that will have you coming back year after year!br*Stairs only. All guests must have the ability to climb stairs.br*No garage parking.brbrBedroom 1: KingbrBedroom 2: QueenbrLiving Area: Queen Sofa SleeperbrbrAdded 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*Pets are allowed, dogs only. Our pet fee is $39 per day/ per pet. Restrictions may apply on weight and breed, please check when making reservation.brbr*Unit is on the second floors, must be able to climb stairs.brbr*Minimum Age to Book: 23br*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: $500

Apartment

Live the Dream in this 2 Bed/1 Bath Home Steps from Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$327.93

Johnnys Island Palm – Walkable South Siesta Key Condo with Pool & Beach Accessbrbr ️ Why You'll Love This HomebrWelcome to Johnnys Island Palm, a bright and beachy 2-bedroom condo tucked in the heart of South Siesta Key. Just steps from local favorites like the Daiquiri Deck and Captain Curt's, and a short walk to the beach access points along Siesta Key's world-famous white sands. This location lets you park the car and embrace island time. Whether you're soaking up sunsets or exploring by boat, it's the ideal blend of laid-back ease and coastal adventure.brbr ‍ ‍ Perfect ForbrCouples, small families, or friends looking for a casual beach getaway with walkable access to dining, boating, and the Gulf shore.brbr ️ Imagine This...brStart your morning with coffee on the private balcony, the soft salt air reminding you that the beach is just a short stroll away. With breakfast spots and fresh juice bars around the corner, your biggest decision might be flip-flops or barefoot. Spend the day beach combing, grabbing lunch at Captain Curt's, or renting a kayak at nearby Siesta Key Marina for a paddle along the intracoastal waterway. After sunset, take a refreshing dip in the community pool or enjoy dinner on the balcony under the glow of string lights and warm breezes.brbr Where You'll Sleepbr• Bedroom 1: King Bed (1), Ensuite Bathroom with Walk-In Shower, Balcony Access, Smart TVbr• Bedroom 2: Queen Beds (2), Shared Hall Bathroom with Shower/Tub Combo, Smart TVbr• Bonus Space: Sleeper Sofa in Living Roombrbr Explore the AreabrWalk just 0.2 miles to Siesta Key Marina, 0.1 miles to restaurants like Captain Curt's and The Daiquiri Deck, and 0.3 miles to the nearest public beach access point on Siesta Key's award-winning shores. Rent a bike or trolley to explore the island, or head just 7.5 miles to downtown Sarasota for art, culture, and bay front dining.brbr Book Your Island Escape Today!brJohnnys Island Palm offers the best of island life with the comforts of home. With walkable dining, easy beach access, and resort-style shared amenities, it's a perfect South Siesta Key escape. Your stay includes the assurance of a well-prepared condo, so you can settle in and start relaxing from the moment you arrive.brbr Need to KnowbrThis is a condo unit located in a shared building. Guests have access to a shared outdoor pool and common areas. Boat mooring is available on a first-come, first-served basis at the complex. This home shares walls and building space with other units. Free high-speed WiFi. Starter supplies of kitchen and toiletry essentials are provided.

Johnnys Island Palm | Walk to Siesta Key Beach, Marina, Dining & Pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$291.66

Welcome to Prime-Time on Siesta Key! You will LOVE the convenience here: a very short walk to Siesta Beach or Siesta Village in no time at all. No car needed! Almost 1000 sf, this two-level home sleeps 4 comfortably. Two full baths and two bedrooms each with TVs along with a roomy upstairs living area. Laundry room with fully-stocked kitchen, linens, towels, etc. Nice Large backyard and covered parking space.brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrEnjoy Siesta Key in this historic and simple (and very clean) single-level home. Location is wonderful with the area very safe and quiet. Self Check-in/check-out.

Apartment

Steps to the Beach, Short Walk to the Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$288.5

Welcome to Prime-Time on Siesta Key! You will LOVE the convenience here: a very short walk to Siesta Beach or Siesta Village in no time at all. No car needed! Almost 1000 sf, this two-level home sleeps 4 comfortably. Two full baths and two bedrooms each with TVs along with a roomy upstairs living area. Laundry room with fully-stocked kitchen, linens, towels, etc. Nice Large backyard and covered parking space.brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrEnjoy Siesta Key in this historic and simple (and very clean) townhome-style home. Location is wonderful with the area very safe and quiet. Self Check-in/check-out.brbrI am here for you during your stay, but our level of interaction is up to you. I'm only a phone call or text away. You will will be able to self-check-in upon arrival.brbrWalk, Uber, Multiple trolley services available.

Historic & Lovely ❤ Walk to the Beach or Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$298.19

Aloha Kai #34brbrA 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 #34. This charming beach 1-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. Thoughtfully designed 1-bedroom home, featuring a cozy front patio/sunroom, offering a bright and inviting space to relax after a day in the sun, Aloha Kai #34 invites you to kick off your shoes, sip morning coffee on your private front sunroom, and dive into a world of relaxation and adventure. Here's what makes this home so special:brbrBedding Arrangement:br1 Bedroom:brMaster Bedroom with Queen-size bed, Smart TVbrAdditional Sleep: Sleeper Sofa in the Living RoombrTop Features:brSleeps 4brLargest 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 Patio/Sunroom: Sip coffee in the mornings or curl up with a good book in the enclosed sunroom. 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 #34 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 #34 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.

Beachfront Bliss for 4 with Sunroom & Pool Access on Siesta Key - Aloha Kai #34

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$341.7

Aloha Kai #49brbrA 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 #49. This charming beach 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. Featuring two comfortable bedrooms and accommodating up to six guests, making it ideal for travelers seeking a simple and relaxing stay close to the beach, Aloha Kai #49 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure.brbrBedding Arrangement:br2 Bedrooms:brMaster Bedroom with King-size bed and Smart TVbrGuest Bedroom with Two Twin-size beds and Smart TVbrAdditional Sleep: Sleeper 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.brFront Patio: Enjoy morning coffee in the fresh air from your front patio before heading out for the day's adventures.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 #49 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 #49 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.

Beachside Escape for 6 with Pool & Direct Sand Access – Aloha Kai #49

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$326.13

Experience the modern design and relaxing comfort of this newly renovated 2BR 2Bath quadplex unit, just a few mins from sun-soaked Siesta Key Beach, tasty restaurants, exciting shops, parks, attractions, and landmarks. To top it all off is the shared yard with the dreamy swimming pool and lounges, creating a peaceful relaxation haven.brbr✔ 2 Comfy BRsbr✔ Open Design Livingbr✔ Full Kitchenbr✔ Smart TVsbr✔ High-Speed Wi-Fibr✔ Quadplex Amenities (Pool, BBQ, Lounges, Washer/Dryer, Parking)brbrSee more below!brbr---The space---brbrWe take great pride in welcoming you to the recently renovated quadplex unit, where abundant natural light enhances the contemporary design. It boasts a spacious interior and a dreamy patio overlooking the backyard and the stunning swimming pool.brbrThe entire home is furnished with modern amenities and tasteful decoration. Elegant furniture and details dominate the space and are highlighted by rays of healthy sunlight during the day and cozy lighting in the evening. Tiled floors and carefully chosen decor add to the warm and stylish ambiance.brbrHave hours of fun in the open-concept design living area featuring the entertaining living room, fully-equipped kitchen, and dining area, or retreat to two relaxing bedrooms, allowing you to rest and recharge after a day of Gulf Coast adventures.brbrLet’s take a more detailed dive into the amenities and spaces of this modern home.brbr★ LIVING ROOM ★brStep right into the open floor-plan living area with polished tiled floors, where you will find everything needed to create fun, memorable moments during your visit to Siesta Key, FL. brbr✔ Comfortable Sofa, Loveseat and Window Seating Nook with Pillowsbr✔ Smart TV with Rokubr✔ Cozy Sofa Chairbr✔ Coffee Tables & Reading Lampsbrbr★ KITCHEN & DINING ★brThe entire contemporary open floor plan is designed so you don’t miss a single moment of fun. State-of-the-art appliances and granite countertops with a central kitchen bar will quickly make you feel like a 3* Michelin chef while preparing homemade delicacies for your family and friends.brbr✔ Microwavebr✔ Stovebr✔ Ovenbr✔ Toasterbr✔ Blenderbr✔ Coffee Makerbr✔ Refrigerator/Freezerbr✔ Dishwasherbr✔ Sink - Hot & Cold Waterbr✔ Platesbr✔ Glassesbr✔ Silverwarebr✔ Pots & PansbrbrServe your delicious creations on the dining table with unique seating and savor tasty homemade meals with your loved ones. The spacious kitchen bar offers an ideal setting for an early morning breakfast.brbr✔ Dining Table with Seating for 6br✔ Kitchen Bar with Seating for 3brbr★ SLEEPING ARRANGEMENTS – 2 BEDROOMS ★brTake your pick from two highly comfortable bedrooms that can be found in the home. The second bedroom will appeal to children as it boasts a fun bunk bed.brbr♛ Master Bedroom: King-Size Bed, Juliette Balcony, Ensuite Bathroombr♛ Bedroom 2: Queen-Size Bed + Bunk Bed (Twin over Twin)br♛ Living Room: Queen Sofa BedbrbrBoth bedrooms are equipped with a similar set of amenities.brbr✔ Premium Pillows, Linens, and Sheetsbr✔ Smart TVsbr✔ Closets with Hangers and Shelvesbr✔ Dressers with Spacious Drawersbr✔ Night Stands with Reading Lightsbrbr★ BATHROOMS ★brThe gorgeous getaway boasts two full bathrooms stocked with premium essentials, so you don't have to worry about buying/bringing your own. brbr✔ Bathtub with a Showerbr✔ Vanitybr✔ Mirrorbr✔ Toiletbr✔ Towelsbr✔ Hair Dryerbr✔ Essential Toiletriesbrbr★ SWIMMING POOL & PATIO ★brTake in the tranquility and the laid-back Florida lifestyle by unwinding next to the shared swimming pool while the designated BBQ master prepares delicious meals on the grill.brbr✔ Luxury Heated Swimming Poolbr✔ Sun Loungesbr✔ Dining Tables with Parasolsbr✔ Gas BBQ GrillbrbrSecure your reservation today and immerse yourself in the beauty and serenity of Florida's Gulf Coast.brbr---Guest access--- brbrThe unit is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home. The backyard and the pool area are shared with the other guests of the quadplex.brbrOther than the already mentioned amenities, our home also comes with the following:brbr✔ High-Speed Wi-Fibr✔ Self Check-In (Smart Lock)br✔ Travel Crib (available upon request)br✔ Air Conditioningbr✔ Heatingbr✔ Iron/Boardbr✔ Washer/Dryer (in the Building)br✔ Beach Accessories (Chairs, Wagon, and Umbrella)br✔ Free Parkingbrbr---Other things to note---brbr★ ADDITIONAL ACCOMMODATION ★brTraveling in a larger group, or your preferred dates are already taken You'll be happy we offer additional accommodation in the quadplex and the area. Feel free to browse our profile for a detailed list of fantastic stays.brbr★ CLEANING & SANITIZATION ★brHealth, safety, and well-being of our guests are of utmost importance. For this reason, we use a thorough cleaning process after each check-out.brbr★ NO PETS ALLOWED ★brWe love those little (and not so little) furry bundles of joy. Sadly, our home is not suitable to accommodate them.brbr★ NO SMOKING INSIDE ★brPlease refrain from smoking inside the home! Any smoking evidence will result in a fee for odor removal and furniture cleaning.brbr★ NO PARTIES/EVENTS ★brWe kindly ask you to treat our home as your own to preserve its pristine condition for future guests and your return visits.brbrThank you very much for your understanding.brbr---Interaction with guests--- brbrWe will be accessible 24/7 for our guests via phone, text, or the VRBO app. brExpect a quick and prompt response. We give our guests space but are available for every inquiry. brbrContact us now so we can begin arranging your perfect vacation!brbr---The neighborhood---brbrThe quadplex is on a private street with a gated beach access point in Siesta Key, a tropical haven on the west coast of Florida that embodies the essence of paradise—known for its powdery white sands, crystal-clear waters, and laid-back atmosphere.brbrSiesta Key is renowned for having some of the most breathtaking beaches in the United States. Siesta Beach, in particular, has earned acclaim for its powdery, quartz-crystal sands, which stay cool even on the warmest days. Sunset at Siesta Beach is a spectacle not to be missed, with hues of orange and pink painting the sky as the sun dips below the horizon.brbrBeyond the beaches, Siesta Key offers a wide range of outdoor activities. Kayak through the calm waters of the mangrove tunnels at South Lido County Park, paddleboarding in the Gulf of Mexico, or embark on a fishing charter to catch your dinner. Nature enthusiasts will appreciate the lush landscapes and wildlife in the nearby Myakka River State Park.brbrSiesta Key Village is the heart of the island's dining, shopping, and entertainment scene. Stroll along quaint streets with boutiques, surf shops, and art galleries. Savor fresh seafood at beachfront restaurants, sip tropical cocktails at vibrant bars, and enjoy live music under the stars.brbrThe warm waters surrounding Siesta Key beckon adventure seekers to explore. Try windsurfing, jet skiing, or parasailing for an adrenaline rush. Scuba diving and snorkeling enthusiasts will be delighted by the vibrant underwater world of the Gulf. For a more leisurely experience, rent a boat, explore the Intracoastal Waterway, or take a dolphin-watching tour.brbrCome and discover the beauty and tranquility of this coastal gem, where every day feels like a beach day in paradise.brbrHere are some places of interest you'll be looking to visit during your stay.brbr✔ PARASAIL SIESTA (2 min away)br✔ Siesta Key Beach (2 min away)br✔ Crescent Beach (2 min away)br✔ Siesta Key Watersports (4 min away)br✔ Siesta Key Village (5 min away)br✔ Marie Selby Botanical Gardens (14 min away)br✔ Sarasota Jungle Gardens (24 min away)br✔ Lido Key Beach (24 min away)br✔ South Lido County Park (25 min away)br✔ Mote Marine Laboratory & Aquarium (26 min away)br✔ St. Petersburg (55 min away)br✔ Tampa (1h 5 min away)br✔ Fort Myers (1h 18 min away)brbr***Distance times are calculated if traveling by car.brbrGetting aroundbrbrIf you arrive by car, you will be happy to know that we offer free parking. However, if you would like to avoid driving during your stay, there are many convenient, easily accessible transportation options close to our home.brbr✔ Siesta Key Breeze Trolley (stop on top of the street leads you to Siesta Key Village for free)br✔ Taxibr✔ Lyft & UberbrbrIf you are flying in/out of the area, the best way would be at the below airport:brbr✔ Sarasota Bradenton International Airport (25 min away)br

Bright & Modern ~ Heated Pool ~ Gated Beach ~ Pkg!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$323.07

This 2-bedroom, 2-bathroom condo is the perfect place to take your next vacation! With a queen bed in the Master bedroom, two twins beds in the second bedroom, and a sleeper sofa, this condo can comfortably sleep up to 6 guests. You will be amazed by the breathtaking Siesta Key sunsets from the large balcony! This unit is on the 2nd floor, accessible by stairs or elevator. This location has something for everyone, Our House at the Beach offers guests a heated pool, tennis courts and a covered pavilion with grilling area. Right across the street is our world-famous Siesta Beach, and just minutes away is Siesta Key Village, offering endless boutique shopping, live entertainment, and dining, making this condo the perfect place for you to enjoy your island getaway vacation! brbrBedroom 1- QueenbrBedroom 2- Two twinsbrLiving Room – 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: 25br*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

Stunning Sunset view! 2Bed, 2 bath on Siesta Key

Siesta Key, Florida, United States

3

Bed

Bath

6

Sleeps

$188.28

Harbor Towers Unit 614 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers Unit 614, a beautifully positioned sixth-floor two-bedroom, two-bathroom condo in one of Siesta Key’s most desirable gated waterfront communities. Perfect for extended stays with a 13-night minimum requirement, this spacious retreat offers peaceful water views, comfortable coastal interiors, and resort style amenities just minutes from Siesta Key Beach and Siesta Key Village.brbrHighlightsbr• 2 Bedroom / 2 Bathroom condobr• King, 2 Twin beds, Queen sleeper sofabr• 13-night minimum stay communitybr• Sixth-floor water and lake viewsbr• Private balconybr• Short drive to Siesta Key Beachbr• Gated waterfront communitybr• 2 heated community poolsbr• 3 Har-Tru tennis courtsbr• 40-slip marinabrbrHarbor Towers is known for offering amenities rarely found in many Siesta Key associations. Guests enjoy two heated pools surrounded by tropical landscaping, three tennis courts, and a 40-slip marina with direct access to the Intracoastal Waterway. The gated community also includes a fitness center and sauna, making it especially appealing for snowbirds and extended stay guests seeking both relaxation and recreation.brbrUnit 614’s private balcony showcases serene waterfront views, providing the perfect spot for morning coffee or quiet evenings overlooking the beautifully maintained grounds. The open living and dining area is bright and welcoming, with large windows that bring in natural light and frame the surrounding views. Comfortable seating and a television create a relaxed atmosphere for unwinding after a day at Siesta Key Beach. The kitchen features warm wood cabinetry, granite countertops, and full-size appliances, offering everything needed for preparing meals during your stay. The adjacent dining space provides a cozy setting for shared dinners and conversation.brbrThe primary bedroom features a king bed, soft coastal decor, and direct access to the ensuite bathroom with a spacious vanity and shower and tub combination. The second bedroom includes two twin beds, making it ideal for family or visiting guests. A hallway bathroom with a shower and tub combination adds convenience and flexibility for groups. The living room includes a queen sleeper sofa, providing additional sleeping space when needed.brbrRoom Details:br-Primary Bedroom: King bed and ensuite bathroom with shower and tub combinationbr-Second Bedroom: Two twin bedsbr-Living Room: Queen sleeper sofabr-Hallway Bathroom: Shower and tub combinationbrbrHarbor Towers Unit 614 includes elevator access, assigned parking, community grilling areas, and beautifully maintained tropical grounds. The 13-night minimum stay requirement creates a quieter, more residential atmosphere ideal for seasonal guests, families, and remote workers.brbrIf you are searching for a Siesta Key condo rental with water views, resort style amenities, and the comfort of an extended stay community, Harbor Towers Unit 614 by Tropical Sands Accommodations is the perfect choice. Secure your preferred dates today and enjoy elevated coastal living in beautiful Siesta Key.

Harbor Towers 614 - Tropical Sands Accommodations

Siesta Key, Florida, United States

1

Bed

1

Bath

Sleeps

$350.12

Amenitiesbr•Panoramic bay views from a spacious private condobr•Open floor plan with updated furnishingsbr•Fully stocked kitchen with modern appliancesbr•Comfortable living area with couch, loveseat, and two reclinersbr•Primary bedroom with poster bed, SMART TV, and ensuite bathroombr•Guest bedroom with two queen beds, SMART TV, and ensuite bathroombr•High-end mattresses and soft linens for restful sleepbr•Two full bathrooms with large walk-in showers and spacious vanitiesbr•Hallway powder room for guestsbr•Full-size washer and dryerbr•Beach chairs and beach equipmentbr•Access to Island Reef community amenitiesbr•Two heated swimming pools (open until 10 pm)br•Tennis and pickleball courtsbr•Fitness centersbr•Library, billiards room, and game roombr•Shuffleboard courtsbr•Bay and Gulf side grilling patiosbr•Short boardwalk access to Turtle BeachbrbrWelcome to your relaxing coastal escape at Island Reef on beautiful Siesta Key, located near the peaceful shoreline of Turtle Beach. This spacious bayfront condo offers panoramic water views and a calm, breezy setting perfect for enjoying the laid-back island lifestyle.brbrInside, the condo features an inviting open floor plan designed for both comfort and connection. The nicely updated living area offers several places to unwind after a day at the beach, including a comfortable couch, two plush recliners, and a loveseat. Large windows invite natural light while showcasing the beautiful bay views that make this location so special. The fully stocked kitchen provides everything needed to prepare anything from quick breakfasts to full dinners with family and friends.brbrThe sleeping accommodations are thoughtfully designed to ensure restful nights. The primary bedroom features a beautiful poster bed, a SMART TV, and a private ensuite bathroom. High-end mattresses and soft linens create a comfortable retreat where you can recharge for another day on the island. The guest bedroom is ideal for families or friends traveling together, offering two queen beds, a SMART TV, and its own ensuite bathroom.brbrBoth full bathrooms are spacious and updated with large walk-in showers, generous vanities, and plush towels that add a spa-like touch. A convenient hallway powder room is perfect when entertaining guests. A full-size washer and dryer in the condo provides added convenience during your stay, and beach chairs and equipment make your trips to the shore effortless.brbrIsland Reef offers outstanding resort-style amenities. Guests can enjoy two heated swimming pools, one located on each side of the community, with plenty of loungers, tables, and chairs for relaxing poolside. The beach is easily reached via a short boardwalk located just beyond the Gulf-side pool.brbrCommunity amenities also include tennis and pickleball courts, fitness centers, shuffleboard courts, grilling patios on both the bay and Gulf sides, and a library, billiards room, and game room. The bayside dock, fishing pier, and kayak launch are currently closed for hurricane repairs and are expected to reopen in May 2026.

Bay Front Views! Pool, Tennis, Gym, Fishing Dock & Beach Access

Siesta Key, Florida, United States

Bed