Vacation Condo Rentals By Owner In Siesta Key, FL

Welcome to the fabulous Condo 209 at Crescent Royale! This condo features 1-bedroom, 1-bathroom pad is spacious, boasting over 825 sq. ft. of living space, leaving you plenty of room to spread out and relax.brbrThe Master bedroom is home to a king-sized bed that will make you feel like royalty. And there's no need to worry about a second guest, as this unit is equipped with a sofa sleeperbrbrBeach vibes meet modern decor, making this condo the perfect place to call home while you soak up the sun. Chairs, umbrellas, mat, cooler and beach cart are provided and ready for beach fun as well. But wait, There's more! If you're looking for a break from the sand, hop on the free trolley or take a breezy stroll to the Village, where you'll find fantastic dining, shopping, and nightlife all wrapped up in old Florida charm.brbrAnd if you're looking to unwind without leaving the condo, we've got you covered! Take advantage of the heated pool, fitness center, and BBQ areas right on-site.brbrWhether you're planning a romantic getaway or a relaxing retreat, this condo has got you covered. With our friendly on-site team available 24/7, you can book with confidence and prepare for the ultimate Siesta Key Beach vacation!

Steps to Siesta Key Beach 1 Bed 1 Bath Full Gulf Views

Siesta Key, Florida, United States

Bed

Bath

3

Sleeps

Select Dates for Price

Welcome to your coastal getaway at Whispering Sands!brbr- Spacious 2BR/2BA beachfront condo with a private balcony and modern amenities.br- Ideal for relaxation, accommodating up to 4 guests in comfortable bedrooms.br- Enjoy the refreshing community pool and fully equipped kitchen.br- Steps from stunning Siesta Beach, famous for its powdery white sand.br- Explore vibrant Siesta Key Village, filled with dining and shopping options.brThe spacebrWelcome to our spacious 2-bedroom, 2-bathroom condo located at Whispering Sands, Sarasota, FL. With 1282 square feet of living space, this condo offers plenty of room for your comfort and relaxation.brbrbrThe condo features a private balcony, where you can soak up the sunshine or enjoy your morning coffee with a view. Inside, you'll find a well-appointed living area, perfect for unwinding after a day of exploration.brbrThe two bedrooms provide ample sleeping arrangements with two beds in total, accommodating up to four guests. Each bedroom offers a cozy retreat with comfortable bedding and pleasant decor.brbrbrThe condo also provides one parking space for your convenience, ensuring easy access and peace of mind during your stay.brbrWhether you're looking to explore the beautiful surroundings of Sarasota or simply relax and rejuvenate, our spacious condo is the ideal home base for your vacation. Book now and experience the comfort and convenience of this wonderful retreat.brGuest accessbrAs our valued guest, you will have full access to the entire condo during your stay at Whispering Sands. This includes:brbrLiving Area: Relax in the comfortable seating area and enjoy the entertainment options available, such as a TV and other amenities.brbrKitchen: Feel free to make use of the fully equipped kitchen to prepare meals and snacks. It includes appliances, cookware, and utensils for your convenience.brbrBedrooms: Rest and recharge in the two bedrooms, featuring comfortable beds and cozy furnishings.brbrBathrooms: Enjoy the convenience of two bathrooms, each equipped with essential amenities such as a shower, sink, and toilet.brbrPrivate Balcony: Take advantage of the private balcony, where you can enjoy the fresh air and perhaps catch a glimpse of the beautiful surroundings.brbrAdditionally, you will have access to the common areas and facilities within the condominium complex. Please adhere to any rules or guidelines provided by the management to ensure a pleasant and respectful stay for everyone.brbrbrWe want you to feel at home during your time here and encourage you to make the most of the amenities and space provided for your comfort and enjoyment.brOther things to notebrHere are the important policies and guidelines to note for your stay at Whispering Sands:brbrCheck-in: We facilitate self-check-in, and guests are welcome to check in any time after 4 pmbrbrbrCheck-out: We kindly ask that you check out on or before 10:00 AM on your departure date. This allows us enough time to clean and prepare the property for the next guests.brbrNo Pets Allowed: Unfortunately, pets are not permitted in the condo. We appreciate your understanding and cooperation in adhering to this policy.brbrNo Smoking: Smoking is strictly prohibited inside the condo and within any common areas of the complex. Please respect this policy to maintain a clean and smoke-free environment.brbrNo Parties: The condo is intended for quiet and peaceful stays, and hosting parties or large gatherings is not allowed. Please be considerate of the neighbors and keep noise levels to a minimum, especially during nighttime hours.brbrThese policies are in place to ensure a comfortable and enjoyable experience for all guests and to maintain the integrity of the property.brbrbrIf you have any questions or need further clarification about these policies, please feel free to contact us. We want to ensure that your stay at Whispering Sands is pleasant and in accordance with these guidelines.brbrWhere you’ll be:brNeighborhood highlightsbrWhispering Sands Dr is located in the beautiful neighborhood of Siesta Key in Sarasota, FL. Siesta Key is known for its stunning beaches, vibrant atmosphere, and a wide range of recreational activities. Here's a brief description of the neighborhood:brbrSiesta Beach: Just a short distance away from the condo, Siesta Beach is renowned for its soft, powdery white sand and crystal-clear turquoise waters. Enjoy sunbathing, swimming, beach volleyball, or take a leisurely stroll along the shore to witness breathtaking sunsets.brbrDining and Shopping: Siesta Key offers a diverse selection of dining options, ranging from casual beachfront eateries to upscale restaurants. Indulge in fresh seafood, international cuisine, and local flavors. The area also boasts charming shops and boutiques where you can browse for unique souvenirs, clothing, and more.brbrOutdoor Activities: Embrace the outdoors with various activities available nearby. Explore the mangrove forests and waterways on a kayak or paddleboard adventure. Take a fishing charter to try your luck at catching some local fish. Golf enthusiasts will find several well-maintained golf courses in the vicinity.brbrCultural and Art Scene: Sarasota is renowned for its vibrant arts and culture scene. Visit the Ringling Museum of Art, which houses an impressive collection of European paintings,brQuiet hours 9:00pm – 7:00ambr1282 sq ftbr2 bed 2 bathbrMax of 4 guestsbrMust be 55 and older

Charming waterfront 2-bedroom condo in Siesta Key

Siesta Key, Florida, United States

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Bath

Sleeps

$346.16

Enjoy panoramic Gulf and Siesta Key views from this spacious 2-bedroom, 2-bathroom corner condo, offering over 1,250 sq ft of coastal comfort.brbrInside, you’ll find a gourmet, fully stocked kitchen with an island and granite countertops—perfect for easy meals after a day at the beach. The master bedroom includes two queen beds, while the guest bedroom features a king, providing plenty of room for families or couples traveling together.brbrAs a corner unit, the condo boasts an oversized screened lanai, ideal for savoring sunsets and soaking in the breathtaking views. Beach days are effortless with complimentary chairs, towels, and umbrellas included.brbrLocated directly across the street from America’s #1 Beach—Siesta Key Beach, Crescent Royale puts you steps from powder-soft sand and turquoise waters. Dining, shops, and entertainment are only a short stroll or free trolley ride away. Plus, our onsite staff is here to ensure your stay is seamless from start to finish.brbrBook this condo today for the ultimate beach getaway!

Stunning Gulf Views 2 Bed 2 Bath Sixth Floor at Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$356.32

Get ready to dive into a tropical paradise at Condo 512! This dreamy dwelling boasts drop-dead gorgeous views of The Gulf and Siesta Key Beach from its fourth-floor location, giving you a front-row seat to America's number one beach!brbrWith two bedrooms and two full bathrooms, this 1220 sq ft condo is a slice of heaven on earth! Featuring two queen beds in the master bedroom and an extra queen in the guest room, you're in for a comfy and luxurious stay. And, the fully-equipped kitchen is loaded with all the tools and equipment to whip up delicious meals.brbrFeeling lazy No problem! This condo comes with four flat-screen TVs, basic cable, and free wifi to keep you entertained. Plus, the screened-in lanai lets you soak up the legendary sunsets in style. Crescent Royale, the condo's location, offers a heated pool, workout gym, BBQ area, and shuffleboard court, so you can keep the good times rolling throughout your stay.brbrLocated at the heart of Siesta Key, you're only a hop, skip, and a jump away from Siesta Key Village, where you'll find an abundance of restaurants, nightlife, and souvenir shops to explore. Plus, the on-site management team is on-hand to make sure everything goes smoothly during your stay. Get ready for a vacation you'll never forget!

Sunsets and Sand Siesta Key Beach Top Floor 2 Bed 2 Bath Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$367.77

Enjoy the inviting atmosphere in a comfortable corner condo on the sixth floor with lots of natural light. This condo offers panoramic views of the beaches and gulf. Siesta Key Beach is a public and life guarded. The free trolley ride to the Village can provide dining, nightlife, shopping, people watching and is only a short walk to Patriot Point. The glass enclosed lanai offers four season enjoyment and more living space. The kitchen is well equipped or there are any restaurant choices.brbrThe ultimate vacation destination can be base for many excursions around Siesta Key, Sarasota, and Beyond.

Breathtaking Gulf Views 2 Bed 2 Bath Sixth Floor at Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$197.8

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Harbor Towers 2nd Fl Dock Views! brbr brbrThis fully renovated Harbor Towers condo is less than a 20-minute walk to both Siesta Key Beach and Crescent Beach, making it the ideal location for your next getaway. Enjoy a modern kitchen with state-of-the-art appliances, two spacious bedrooms, updated bathrooms, and a screened-in veranda. Resort-style amenities include two heated pools, Har-Tru tennis courts, a fitness center, boat docks, BBQ areas, and a clubhouse for indoor and outdoor dining. brbr brbrLOCATION HIGHLIGHTS: brbr- Direct bayfront setting on the Intracoastal brbr- Quick 2–3 minute drive or 15-minute walk to Siesta Key Beach brbr- Trolley stop just outside the building brbr- Close to Siesta Key Village dining, shopping, and live music brbr- Resort-style community with marina views and sunrise scenery brbr- 2 heated swimming pools, 3 clay tennis courts brbr- Clubhouse with grilling station, exercise facility, and sauna brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom 2nd floor condo (1152 sq ft) brbr- Screened-in exterior veranda brbr- Dedicated WIFI brbr- Assigned parking spot (1 spot) brbr brbrLIVING ROOM: brbr- Spacious living area, couch doubles as queen sleeper brbr- Smart TV brbr- Access to veranda brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with stainless steel appliances brbr- Dining area seats 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, walk-in closet, smart TV brbr- Master ensuite bathroom: spacious vanity with walk-in shower brbr- Guest bedroom: queen bed, smart TV brbr- Guest ensuite bathroom: tub/shower combo, separate vanity area brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. brbr brbrLOCAL FAVORITES: brbrSiesta Key Beach with powder-white sand and turquoise water brbrSiesta Key Village restaurants, bars, and boutique shops brbrTrolley rides to the beach and village hotspots brbr brbrIMPORTANT INFO: brbr- Quiet hours enforced by the community brbr- No parties or smoking allowed brbr- Only 1 parking spot. Parking restrictions: no trailers, oversized vehicles, boats, or commercial vehicles. No Motorized Carts or Scooters Allowed brbr brbrDISCOVER WHY GUESTS KEEP COMING BACK. LOCK YOUR SIESTA KEY ESCAPE TODAY!brbrPlease note, each unit is only allowed 1 parking spot. brbr brbrStarting June 1st, the complex has scheduled a roof repair. They are expecting to be done in 4-5 weeks (weather permitting). brbrCrane will be up front. Carport repairs will take place starting June 8, 2026. Please use caution around work areas. Thanks for your understanding.brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Fully Renovated on the Bay, Heated Pool, Tennis, Fishing, Screened Balcony

Siesta Key, Florida, United States

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Bath

Sleeps

$214.48

Spending time in Siesta Key is always an exciting experience. However, those who choose to book a stay in Holiday House 2 will find that accessing those area highlights you can't wait to explore is easier than ever! This inviting 1-bed, 1-bath home away from home can easily accommodate up to 4 guests at a time and sits just step from Siesta Key Beach. It's an ideal retreat for those who are traveling this way as a couple, or in a small group of family and friends. When you can't wait to enjoy a stay that brings comfort, quality, and convenience into every aspect of your getaway, Holiday House 2 checks every box on the list.brbrInterior AmenitiesbrbrStepping into Holiday House 2, guests will find a bright, welcoming, and stylish space waiting to greet them. This property enjoys an open floor plan as well as large windows throughout to enhance the view and access to natural light flow during those sunny Florida days. The living room in Holiday House 2 is a cozy place to settle into style. The room features a leather sofa topped with colorful chevron throw pillows. When entertainment is top of mind, make the most of the TV mounted on the wall in the living room with streaming entertainment. brbrThe living room opens up to the dining area and kitchen where guests are free to serve up home-style meals on a whim. The kitchen showcases spacious and sleek black counters as well as custom white cabinetry filled with cookware and a collection of stainless-steel appliances. The decorative black, white, and gray tiled backsplash brings a modern aesthetic touch into this space.brbrWhen it's time to rest up after a day of Siesta Key fun, guests will find the bedroom in this property an oasis of rest and relaxation. This room features a queen-size Casper mattress, two nigh stands, and a closet for clothing.brbrTwin size roll-a-way beds are available in the unit for guests 3 and 4.brbrWasher and dryer are available just around the corner from the unit (in the same building, by your parking space) free for guest use. brbrExterior FeaturesbrbrWhen you're looking for outdoor fun without traveling anywhere at all, Holiday House 2 has you covered. This home hosts a charming, screened patio with outdoor table furnishings that can be accessed off the living room. This patio provides a view out over the property's shared heated pool where guests can enjoy a swim or settle into one of the loungers. Outside, guests can also enjoy an alfresco meal thanks to the BBQ grill near the pool and surroundings that are lush with tropical foliage.brbrBook TodaybrbrWhen you're ready to enjoy Siesta Key, the team at Rent Siesta Key has the accommodations you need to make it an amazing stay. Have questions Send us a message — we'd love to help you plan your stay!

Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach

Siesta Key, Florida, United States

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Bath

Sleeps

$218.93

Making the most of a sunny getaway starts with booking Holiday House 1 the next time travel plans bring you to scenic Siesta Key. This inviting 1-bedroom, 1-bath abode is a welcoming place for up to 4 guests at a time to enjoy. Whether you're headed here with family, friends, or a significant other, Holiday House 1 puts you in the heart of the Florida fun. This property is just a walk away from the sandy shores of Siesta Key Beach and provides impeccable amenities to enjoy when you're cozied up inside as well!brbrInterior AmenitiesbrbrHoliday House 1 is a wonderful retreat for those looking for a place to enjoy in Siesta Key that seamlessly pairs comfort and convenience. This home away from home enjoys an open floor plan, creating an enhanced sense of space throughout. Guests will also appreciate the large windows that allow for ample natural light flow and a great view too. The living room in Holiday House 1 hosts a leather sofa in front of a TV with streaming services for added entertainment value. Large sliding glass doors lead out to the screened deck area.brbrThe kitchen in Holiday House 1 is a fully equipped space where guests can serve up breakfast, lunch, or dinner with ease. This culinary area includes sleek black countertops matched up with custom white cabinetry stocked with cookware. The collection of stainless-steel appliances in the kitchen is complement by the gray, white, and black tile backsplash beautifully. When it's time to enjoy a meal, guests can easily gather around the table for four topped with greenery that sits between the kitchen and living room.brbrWhen it's time to rest up after a day of fun, the bedroom in this property is an oasis of tranquility. Here, guests can fall asleep on a queen-size Casper mattress. Ample dresser and closet space.brbrTwin size roll-a-way beds are available in the unit for guests 3 and 4.brbrWasher and dryer are available just around the corner from your unit (in the same building, by your parking space), free for guest use. brbrExterior FeaturesbrbrWhile exploring Siesta Key is a must, Holiday House 1 also has plenty of on-site options for outdoor fun to enjoy. Guests can move through the sliding glass doors in the living room to reach the screened-in patio complete with a table and chairs. This space offers up a view of the property's shared pool whose deck is dotted with cozy loungers. The outdoor pool area is surrounded by tropical foliage and also enjoys a grill for those moments when an alfresco meal would hit the spot!brbrBook Your Siesta Key AdventurebrbrThere's no reason to wait when you're ready to enjoy a Siesta Key adventure. Have questions Send us a message — we'd love to help you plan your stay!

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Siesta Key, Florida, United States

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Bath

Sleeps

$269.93

Come and enjoy this two bedroom two bathroom condo style vacation rental located just a short walk to Siesta Key beach. The main living area has an open concept with living room and dining area in the first great room when you enter the unit. There is a full kitchen with breakfast bar opening off to the side of the dining room. The living room is equipped with a flat screen TV and has large glass sliding doors opening out to the screened balcony. The master bedroom is furnished with a king-size bed and TV and has an ensuite bathroom. The guest bedroom is furnished with two twin-size beds and TV. The backyard of this property has a large heated pool, plenty of sun bathing spots, and a BBQ area. there are two twin-size rollaway beds available for guests. Free high speed WiFi is available throughout the property including the pool area. brbrMinimum Reservation Requirement: 1 week minimum Saturday to Saturday during peak season.

Siesta Key Beachside Vacation Rental W/ Heated Pool – Walk to Beach and More

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$208.14

Taking time to kick back and relax in beach-focused style is easy to do when you make your way to Siesta Key and book One Ocean-B to complete your adventure. This welcoming and colorful 2-bed, 1-bath home away from home is designed to welcome up to 4 guests at a time making it an amazing choice whether you're enjoying a Florida getaway with family or spending time with a group of close friends. One Ocean-B provides amazing amenities for guests to enjoy but also has the prime location to match. This property is only a block from the beach, within walking distance of great shops and restaurants and in proximity to Stickney Point Bridge as well. brbrInterior AmenitiesbrbrStepping into One Ocean-B, this open concept floorplan makes it simple for guests to move between living, dining, entertainment, and sleeping areas during their stay. The property also enjoys large windows throughout that frame a lush view and allow ample light flow into the home. brbrThe living room in One Ocean-B features a sofa and an armchair for guests to settle into as well. The furnishing set is situated behind a coffee table as well as a flat-screen television that's positioned against the far wall. The living room opens up seamlessly to the kitchen and dining area where guests are invited to savor a home-cooked meal when they aren't exploring local restaurants. The kitchen hosts a collection of stainless-steel appliances, spacious counters, white custom cabinetry and a full brick-tiled backsplash too. The dining room table for four sits around the corner from the kitchen just next to the living room when it's time to gather and enjoy a meal together.brbrWhen it's time to rest, each bedroom in this home makes getting a good night's sleep a breeze. The master bedroom enjoys a queen bed while the second bedroom hosts two twin options. brbrExterior FeaturesbrbrOn days when guests aren't out at the beach, One Ocean-B has plenty to offer in the way of outdoor fun right on-site. This property hosts a charming outdoor patio and adorned with a table and chair set for evenings when an alfresco meal would hit the spot. brbrBook Your Getaway TodaybrbrMake the most of every vacation moment by letting Rest Siesta Key handle your accommodations. Have questions Send us a message — we'd love to help you plan your stay!brbrMINIMUM STAY REQUIREMENTS: 1 week minimum reservation required Saturday to Saturday during peak and summer seasons.

Renovated condo with easy beach access on Siesta

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$336.62

Gulf and Bay Club Unit E701 by Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit E701, a beautiful 2-bedroom, 2-bath condo located within the premier Gulf and Bay Club community on Siesta Key. Perfect for extended stays, this 28-night minimum rental combines the comforts of home with resort-style amenities, all just steps from the award-winning Siesta Beach, known for its soft white quartz sand and crystal Gulf waters. Guests will enjoy access to multiple heated pools, tennis and pickleball courts, and a fully equipped fitness center, all within a gated community designed for relaxation and recreation.brbrHighlightsbr• Located within Gulf and Bay Club on Siesta Keybr• 2 Bedrooms / 2 Bathroomsbr• 2 Queen Bedsbr• 28-Night Minimum Staybr• Shared Heated Pools and Hot Tubsbr• Shared Fitness Center, Tennis, and Pickleball Courtsbr• Shared Shuffleboard and Cornholebr• Washer and Dryerbr• One Assigned Parking Spacebr• Steps to Siesta BeachbrbrEnjoy the best of Siesta Key by resort living with Gulf and Bay Club’s incredible community features! Spend your mornings strolling along Siesta Beach, then unwind by one of the three heated pools or soak in a relaxing hot tub. Stay active with tennis, pickleball, and shuffleboard, or meet neighbors in the spacious clubhouse and recreation room. The beautifully landscaped grounds, serene lagoon views, and private beach access make this community one of the island’s most desirable destinations.brbrThe fully equipped kitchen includes modern appliances, refrigerator, stove, oven, dishwasher, Keurig coffeemaker, toaster, and microwave. Making it easy to prepare meals or enjoy your morning coffee before heading to the beach. The dining area comfortably seats four for family meals or casual gatherings.brbrThe primary bedroom suite offers a relaxing retreat with a comfortable queen bed, ample closet space, and an ensuite bathroom featuring a walk-in shower and dual vanity sinks. The second bedroom also includes a queen bed and easy access to the hallway bathroom with a shower and tub combination. Both bedrooms are designed for restful nights after long beach days.brbrbrRoom Detailsbr• Primary Bedroom: Queen bed, ensuite bathroom with walk-in shower and dual vanitiesbr• Second Bedroom: Queen bed, hallway bath with shower and tub combinationbrbrbrFor your convenience, this condo includes a washer and dryer and one assigned parking space. Guests also have access to the community clubhouse, which features a fitness center, social spaces, and recreational areas ideal for long-term stays.brbrExperience the best of Siesta Key living at Gulf and Bay Club Unit E701, where coastal comfort meets resort convenience. With unbeatable community amenities and a prime location near shopping, dining, and Siesta Village, this condo is your perfect home away from home. Book your stay today with Tropical Sands Accommodations and start your island escape!

Gulf Holiday-E701- Resort-Style amenities!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$456.72

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWELCOME TO JAMAICA ROYALE – UPDATED 2-BEDROOM VILLA brbr brbrEscape to Jamaica Royale, a beautifully updated 2-bedroom villa on picturesque Siesta Key. Offering all the comforts of home with modern upgrades, this spacious villa is just steps from the soft white sands and clear waters of the Gulf of Mexico. Guests enjoy exclusive access to a private beach, three heated pools, and a variety of resort-style amenities—all within a short walk. brbr brbrPROPERTY HIGHLIGHTS brbrMaster bedroom with king bed and ensuite bathroom (tub/shower combo) brbrGuest bedroom with two queen beds and ample storage, ideal for families or groups brbrLiving room with queen sleeper sofa, modern chairs, and flat-screen TV brbrFully equipped kitchen with stainless steel appliances, granite countertops, and bar seating for four brbrPrivate lanai with peaceful garden views, perfect for morning coffee or evening relaxation brbrCovered parking space conveniently located near the villa entrance brbr brbrSLEEPING ARRANGEMENTS brbrMaster Bedroom: King bed + ensuite bathroom brbrGuest Bedroom: Two queen beds brbrLiving Room: Queen sleeper sofa brbrAccommodates up to 8 guests brbr brbrRESORT-STYLE AMENITIES brbrThree heated swimming pools brbrTwo shuffleboard courts brbrBBQ grills and outdoor dining areas brbrOutdoor showers to rinse off after the beach brbrPrivate beach access with plenty of space to spread out brbr brbrLOCATION brbrSteps to the beach via Jamaica Royale’s private access brbr1.5 miles to Siesta Key Village with dining, shopping, and nightlife brbrLocal favorites include Meaney’s Mini Donuts and Big Olaf’s Ice Cream for sweet treats brbrEasy access to free local ride services for hassle-free island transportation brbr brbrADDITIONAL DETAILS brbrNon-smoking, pet-free complex brbrComplimentary Xplorie activities for stays under 28 days, including daily admission to bike rentals, dolphin cruises, kayak rentals, or The Ringling Museum brbrOne complimentary round-trip airport transfer for up to 3 guests from SRQ or TPA with advance reservation (tips appreciated) brbr brbr brbrRelax, unwind, and make lasting memories at this updated villa with modern comforts, private beach access, and the perfect Siesta Key location.brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Jamaica Royale 2BR Villa: Steps to Private Beach & 3 Heated Pools - Daily VIP Perks!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$184.7

Completely updated 2 bedroom 1 bath gulf view villa in Sandy Cove. This is a quiet ground floor unit with a loft, and no one above. The unit has a North West facing view of the Gulf from every room. The master bedroom, bathroom, living room and kitchen are down stairs. Upstairs above the master is a small bedroom and above the living room is a loft. Both the upstairs bedroom and the loft have trundle beds. The unit sleeps 4 comfortably but can accommodate 6.brbrThis is our personal vacation home and are very particular about the upkeep. We have decorated it with high end furniture and finishes, so we have a lot of pride in our home. We love to sit on our back patio and drink our coffee in the mornings while watching the ocean and listening to the sound of the gentle waves. Its amazing to open all of the windows to smell that salty sea air. There is also a sofa bed downstairs in the living room for any additional guests. My husband loves cooking so our kitchen is fully equipped with every thing you will need for a nice meal. Although there is no laundry in the unit, the club house (which over looks the ocean and has a fishing pier and plenty of lounge seating) has coin laundry, so you can leave your laundry in an relax with a book in the hammock or in a lounge chair under a palm tree. We have a rolling laundry cart for easy laundry transportation.brbrThe village is only a short walk away, where you can enjoy all of the restaurants, shopping, ice cream and nightlife Siesta has to offer. Siesta Key Beach is ranked the #1 beach in the world and is only a short bike ride away. In our complex, we have access to the ocean, an amazing pier for fishing or watching our amazing sunsets. There is also the club house with a common grassy area outside with a hammock for lounging around and listening to the waves.

Gulf View Condo-5 minute walk to village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$285.26

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 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 Condo br* 2 bedrooms / 2 bathroomsbr* Spacious Balcony overlooking Southern Siesta Keybr* Fourth Floor Condo overlooks the Intracoastal Waterway and Southern Siesta Keybr* Fully equipped Kitchen with seating for 6 at the dining tablebr* Beach Supplies include- Beach Cart, 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 (Fourth Floor Condo)brBedroom 1: One King Bed (Attached Bathroom) / Balcony Access 32 TVbrBedroom 2: Two Double Beds (Attached Bathroom) / Balcony Access 32 Smart TVbrbrPool Information:br- Community Poolbr- Heated brbrResort 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 & Kayak 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 2 bedroom, 4th Floor Condo Southern View Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$293.77

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 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.brbrAnchorage Resort Condobr2 bedrooms / 2 bathroomsbrSpacious Balcony overlooking Northern Siesta KeybrSecond Floor Condo in the peaceful treetopsbrFully equipped Kitchen with seating for 6 at the dining tablebrBeach Supplies include- Chairs, Cooler, Raft/Float Items, Beach TowelsbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbrDesk & Chairbr25-year minimum age to rent restrictionbrbrBEDROOMS (Second Floor Condo)brBedroom 1: One King Bed (Attached Bathroom) 55 Smart TVbrBedroom 2: Two Queen Beds br* Sleeper Sofa in Living Room *brbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:br* No Hanging Towels over the Balconybr* Lead guest must be age 25 or older. ID is checked upon registration at the resort.br* January 1- April 16 Rentals are 7 nights, beginning and ending on Saturday onlybr* No Pets Allowedbr 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 & Kayak 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. brThis is an industry-standard practice.brbr FOR 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 2 Bedroom Condo 2nd Floor, Community Pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$229.72

Welcome to Bay Oaks C32! Beautifully furnished, 2-floor, 2 bedroom, 2.5 bathroom condo that feels like home. Centrally located to everything Siesta Key. Comfortably sleeps 6 in over 1300sf of living space. Public beach access 1 mile away. Free trolley stops at complex. Private dock. Sauna. Heated pool, club house with pool table, HD cable TV, high-Speed internet. Enjoy excellent dining, boating, parasailing, Sarasota's Ringling Museum, 2 hr drive to Universal, Disney, and Busch Gardens.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.brbrThe spacebrOur ultimate vacation rental in a home that really has it all!brbrThis 2-bedroom, 2.5 bathroom home features all the amenities you can think of for your beach vacation and offers an unbeatable location.brbrThis home can accommodate up to 6 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1)br• Bedroom # 2: Queen Bed (2)brbrExclusive Amenities Include:brbr• Lanai overlooking heated Community poolbr• Fishing Pier and Dockbr• Washer/Dryerbr• Tennis Courtsbr• Clubhouse w/Barbecue Areabr• Dining Tablebr• Secure Covered assigned parking spacebr• Fully-Stocked Kitchenbr• Free Hi-Speed WIFIbr• Free assigned covered parking spacebrbrApprox 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 WorldbrbrGuest accessbrThe pool has quiet hours - after 10PM which is a county rule. This complex closes the pool at that time. No motorcycles and trailers allowed on the complex grounds. One assigned parking space. There are some extra guest spots available on a first come first served basis, but not a large number.

Two-Level, Heated Pool, Trolley to Beach & Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$345.91

Enjoy this darling 1-Bed, 1-Bath condo, located just half a block from the powdery white sand of the world-famous Siesta Key Beach! With a lovely open floor plan, this little home offers a wonderful décor, a kitchenette, a bedroom with a king size bed and a spacious private balcony. Relax by the pool under the warm island sun, or take the quick stroll into the Siesta Key Village for the many great shops and restaurants the island has to offer. Quick walk down the Sunset beach to take in the stunning views and spectacular sun sets. If you feel like venturing off the island, Siesta Key is located just minutes from the downtown area of Sarasota and all it has to offer. Sarasota is the Cultural Gem of the Gulf Coast. It offers numerous galleries, theaters, and some of the finest restaurants in the world. You will not be bored with this location. The list of activities is nearly endless as you can spice up your vacation with bike, kayak, or boat rental for your entertainment. This unit is sure to be a lovely Gulf Holiday for you and your family that will have you returning year after year!brbrThis unit is located on the second floor, stairs only**brbrBedding and Television:brBedroom: Queen, TVbrLiving Room: TVbrbrAdded 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: 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

Cozy 1-Bedroom Steps from Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$405.47

You need a vacation and we've got just the place!brbrNestled amongst two ancient banyan trees, The Little Sandy rests on a quiet tropical street, phenomenally located just one block from the best beach in America! Take a look at the map...we're only 400 feet away from the beach access! brbrNot only are we super-close to the beach, but we're only 1.5 blocks to town...close enough to make it a quick walk, without having to deal with the crowds, all day...and all night!brbrInside, the sun-filled rooms are tastefully decorated in tropical chic. White plantation shutters, sea-foam walls and a southwestern exposure bathes everything in a soft, beautiful sunlight. brbrThere's plenty of space for the kids and the open plan kitchen makes mealtime a breeze. Hi-speed Wi-Fi will keep you in close contact with the rest of the world, but we won't tell anyone if you turn it off! brbrIt can be hard to find a spot for your car on Siesta Key, but we've got you covered with dedicated parking out front. Still, with a location like this, flip-flops are bound to be your preferred method of transport!brbrWhen you're ready to explore, it's just a quick wander down to the soft powder of America's #1 beach for an afternoon of sea and sand. Look out over the turquoise Gulf and dig your toes into Siesta's world-famous quartz sand. brbrIf you feel like staying in, check out the lovely and tranquil pool. It's the perfect place to relax and recharge. brbrRead a novel, finish that screenplay...plan your escape.brbrIn the evening, a hot shower and a short, pleasant walk to the village for drinks, laughs and a great meal. brbrStay out late or stroll back in the moonlight with an ice cream cone. brbrWhatever you choose, lush, high thread-count 100% cotton bedding and a generous assortment of pillows await you. Candlelight, reading light or goodnight, the choice is yours. brbrWe're proud new owners and doing our utmost to create incredible experiences for our guests, so don't let the lack of reviews discourage you. brbrWe'll do whatever it takes to make your holiday one to remember!brbrWe offer a super easy check-in and check-out and know your holiday time is priceless! Wherever possible, we strive to let you arrive early and leave late. Your vacation shouldn't start at 3pm!brbrCelebrating something special Let us know what we can do to help!brbrThe Little Sandy at Siesta Key. Don't you deserve a holiday brbr446 Canal RoadbrSiesta Keybr34242br

The Little Sandy...#1 in Siesta!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1668.87

Summary:brbrDry Dock is a spacious canal-front townhome just a 2-minute walk to Siesta Key Beach . This 6-bedroom, 6.5-bath retreat sleeps 16 and features a private pool & hot tub, shared dock, rooftop deck with Gulf views, elevator, ping pong table, and included kayak & paddle board . Walk to Siesta Key Village for dining and shopping, then relax in modern coastal comfort—perfect for unforgettable group getaways!brbrbrbrThe Space:brbr Dry Dock | Canal-Front Retreat on Siesta Keybrbr 515 Canal Rd Unit B, Siesta Key, FLbrbrbrbrWelcome to Dry Dock, a stunning canal-front townhome just one short block from the powdery white sands of world-famous Siesta Key Beach ️. Designed for memorable group getaways, this spacious retreat pairs modern coastal style with unbeatable amenities—including a shared dock, rooftop deck with sweeping views, and a private pool and hot tub. With an elevator for easy access and Siesta Key Village only steps away, island living doesn’t get easier than this!brbrbrbr✨ Highlightsbrbrbrbr• Canal-front home with dock accessbrbr• ‍♂️ 2-minute walk to Siesta Key Beachbrbr• ‍♀️ Private pool & hot tubbrbr• Rooftop deck with Gulf viewsbrbr• Dog friendly (w/ approval & fee)brbr• Elevatorbrbr• Ping pong tablebrbr• ️ Professional linen programbrbr• Kayak & paddle board includedbrbrbrbr Inside the HomebrbrbrbrSpread over two residential levels above the garage, Dry Dock comfortably sleeps up to 16 guests with six bedrooms and six and a half bathrooms. The open-concept living room features an oversized sectional—perfect for movie nights or reconnecting after a beach day . Step onto the balcony to sip coffee while watching boats glide by on the canal.brbrbrbrThe fully equipped kitchen shines with stainless steel appliances, generous counter space, and a large island with seating for six. A banquet-style dining table seats 12, allowing the entire group to gather, dine, and celebrate together ️.brbrbrbrOutdoors, paradise awaits —an expansive covered patio with an outdoor bar, TV lounge, and ping pong table, plus a sparkling pool and hot tub surrounded by loungers. Launch a kayak or paddle board right from the dock, or head upstairs to the rooftop deck for sunset cocktails and endless Gulf views .brbrbrbr ️ Bedrooms & Sleeping Arrangements (Sleeps 18)brbrbrbr• Primary Bedroom (2nd Level): King bed, ensuite bath with tub/shower combobrbr• Bedroom 2 (3rd Level): King bed, ensuite with walk-in shower & private balconybrbr• Bedroom 3 (3rd Level): King bed, ensuite with walk-in shower, shared canal-view balconybrbr• Bedroom 4 (3rd Level): King bed, ensuite with walk-in shower, shared balconybrbr• Bedroom 5 (3rd Level): Two twin bunk beds, ensuite bath with tub/shower combobrbr• Bedroom 6 (2nd Level): Full-over-full bunk bed, ensuite bath with tub/shower combobrbrbrbrTraveling with a big group ✨ Rent the neighboring townhome, Salty Dog, just next door! With a mirrored layout and shared location, both homes together can comfortably host larger families or groups while still offering everyone space, privacy, and easy island living.brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨

Dry Dock | Canal-Front Retreat on Siesta Key

Siesta Key, Florida, United States

Bed