Vacation Rentals By Owner In Siesta Key, FL

$4029.54

Walk to siesta key

Siesta Key, Florida, United States

Enjoy a peaceful stay at this marvelous 5-bedroom house in Siesta Key.brWe offer 5 bedrooms, 2 bathrooms, family room, full kitchen, laundry, patio, pool and free parking.brJust a few minutes walking to Siesta Key.brWe can accommodate up to 15 people.

5

Bed

2

Bath

15

Sleeps

$500.56

/ Nightly

Condo

Top Floor Views 3 Bedroom 3 Bath at Siesta Key Beach

Siesta Key, Florida, United States

This is your chance to enjoy one of the best views on Siesta Key from the comfort of a spacious 7th-floor penthouse. With 3 bedrooms, 2 bathrooms, and over 1,700 square feet, this beachfront condo offers unmatched Gulf of Mexico vistas and all the space you need for a relaxing coastal escape.brbrWhile the decor and furnishings may be dated, the unit is clean, well-maintained, and priced accordingly. Guests who prioritize spectacular views and prime location over modern upgrades will find exceptional value here. The condo needs to be rennovated and is priced to reflect it's lack of modernization.brbrThe Master Suite features a king-sized bed, with queen beds in the two guest rooms. A fully stocked kitchen, free Wi-Fi, and three flat-screen TVs provide the essentials for a comfortable stay. The unit also includes a full beach kit—chairs, towels, and umbrella—for your days on the sand, just steps away from your front door.brbrEnjoy resort-style amenities at Crescent Royale, including a heated pool, fitness center, BBQ area, shuffleboard, and the convenience of onsite management. Siesta Key Village is just a trolley ride away, offering dining, shopping, and entertainment.brbrBook this rare penthouse today and enjoy million-dollar views at a fraction of the cost.

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Bath

Sleeps

$290.54

/ Nightly

Condo

Modern Siesta Key Beach Retreat 2 Bed 2 Bath Gulf and Beach Views

Siesta Key, Florida, United States

Check out this completely renovated 2nd floor condo! Unit 203 has had a complete facelift! This open floor plan allows beach visibility as soon as you walk in the door. New everything, furniture, TVs, stainless steel appliances, flooring, remodeled bathrooms and kitchen. brbrEnjoy the beach from the lanai with a short walk to the white sands of the incredible Siesta Beach. This condo also includes beach equipment for your convenience: beach chairs, a beach umbrella, beach towels, and a beach wagon. If the beach isn't your thing, take a short elevator ride or get your steps in by taking the stairs down to the heated pool. You will also have a designated parking spot. brbrThe Master and guest suites each have new King size beds, a walk in closet and their own bathroom. Chairs, umbrellas, mat, cooler and beach cart are provided and ready for beach fun as well!brbrWe want to accommodate your vacation needs while being our guest. If you need something, please ask.brbrCome to Siesta Key, with or without your car. It's a short walk to the vibrant Siesta Key Village and all of the cafes, restaurants, bars and shopping. Take the free trolley anywhere on the island as well. Once you're here, you'll never want to leave!

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Bath

Sleeps

$454.7

/ Nightly

Condo

Dramatic Siesta Key Gulf Views 3 Bed 3 Bath Top Floor Steps to Beach

Siesta Key, Florida, United States

Discover the rare opportunity of finding a beachfront high-level condo with three bedrooms on Siesta Key! This stunning property on the fifth floor provides the epitome of luxury living with 1,700 square feet of living space and three bathrooms.brbrUnwind and bask in the breathtaking views of the Gulf of Mexico from the lanai or relax in the plush bedrooms. The gourmet kitchen provides the ultimate comfort of home, while complimentary Wi-Fi and three TVs ensure everyone can stay entertained.brbrThis penthouse is conveniently located just a few steps away from America's best beach and comes with a beach kit including chairs, towels, and an umbrella. You can also enjoy dining and shopping options in Siesta Key Village, which is just a quick trolley ride away.brbrCrescent Royale provides additional luxuries such as a heated pool, gym, BBQ area, and shuffleboard. With onsite management, you can rest assured that your vacation will be comfortable and hassle-free. Don't miss out on this highly sought-after penthouse and experience the ultimate beach lifestyle today!

3

Bed

3

Bath

8

Sleeps

Select Dates for Price

Condo

Charming waterfront 2-bedroom condo in Siesta Key

Siesta Key, Florida, United States

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

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Bath

Sleeps

$346.16

/ Nightly

Condo

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

Siesta Key, Florida, United States

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!

2

Bed

2

Bath

6

Sleeps

$367.77

/ Nightly

Condo

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

Siesta Key, Florida, United States

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.

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Bath

Sleeps

$236.13

/ Nightly

Condo

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

Siesta Key, Florida, United States

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!

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Bath

Sleeps

$356.32

/ Nightly

Condo

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

Siesta Key, Florida, United States

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!

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Bath

Sleeps

$197.8

/ Nightly

Condo

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

Siesta Key, Florida, United States

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.

2

Bed

2

Bath

6

Sleeps

$674.79

/ Nightly

Private Vacation Home

Double Your Beachside Fun - Aloha Kai #34 & #55 - Roelens

Siesta Key, Florida, United States

Aloha Kai #34 & #55 (Combined Villas) br(Across the street from each other) br brA Siesta Key Beachside Bliss Awaits! br brStep into the tropical embrace of Aloha Kai #34 & #55, where the rhythmic charm of Siesta Key and a short stroll to Crescent Beach create a perfect escape. This combined villa duo transforms two homes into a seamless paradise, blending sunlit serenity with island adventure. Aloha Kai #34 & #55 invites you to shed your worries, sip coffee on your private patios, and dive into a world of relaxation—book your island haven today! Here's what makes this home so special:brbrBedding Arrangement: brbrAloha Kai #34: br1 Bedroom: brMaster Suite: Queen-size bed, Smart TV brAdditional Sleep: Sleeper Sofa in the living area brAloha Kai #55: br1 Bedroom: brMaster Suite: King-size bed, Smart TV brAdditional Sleep: Sleeper Sofa in the living area brTop Features: brSleeps 8 brLargest Pools on Siesta Key: Plunge into the expansive, sparkling pools surrounded by large lounging decks with plenty of lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access Points: Just a short walk to the powdery white sands of Crescent Beach, rated #1 in the U.S., with shaded pavilions and lounge chairs for your comfort. brFront Patio/Sunroom: Sip morning coffee or unwind with a book in the bright, enclosed sunroom. brCommunity Amenity Sets: Enjoy shuffleboard, ping pong, and poolside community rooms, plus complimentary beach toys and floats for endless seaside fun. brPerfect Home Base Location: Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for island exploration, with activities for all ages and nature lovers. brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #34 & #55 offers easy access to Crescent Beach, famed for its dazzling quartz sand and emerald waters. Whether you're strolling the 3-mile shoreline, lounging under a shaded pavilion, or savoring breathtaking Gulf sunsets, this villa pair delivers tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be effortless and unforgettable. Book your Siesta Key escape at Aloha Kai #34 & #55 today! brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future! brbrDISCLAIMERS: br10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits. brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property. Every Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

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Sleeps

$435.77

/ Nightly

Private Vacation Home

SHORT WALK TO VILLAGE, BEACH - HEATED POOL - LUSH LANDSCAPING 2 SEPARATE UNITS.

Siesta Key, Florida, United States

Located on the Voted number #1 beach in America famous Siesta Key in Sarasota, Florida, The Magnolia House offers the perfect vacation getaway. Two separate units are on this property at 317 and 319 Canal Rd, one upstairs and one downstairs. Each unit is booked separately, or you can book both units for a private family vacation. We book only weekly from Saturday to Saturday.brRecently renovated in the Tommy Bahama style, The Magnolia House maintains that great 'Old Florida' flair with all of the modern-day amenities our guests expect. brOnce you arrive, simply park the car and let the good life begin. Walk one block to Siesta Key Village for a fresh tropical drink at the Daiquiri Deck, or have some oysters at the Siesta Key Oyster Bar. Ready for the beach The Gulf is only steps away! Need some groceries or some new flip flops You guessed it. Nearby! Don't feel like going anywhere How about a dip in your heated pool brGuests at The Magnolia House have it all! brWe hope you will cherish your Siesta Key beach memories, which many have been made at The Magnolia House for over twenty years. We hope you will join us to create your own!br*A SIGNED CONTRACT IS REQUIRED TO CONFIRM. * EVERYONE MUST BE 25 YEARS OR OLDER OR ACCOMPANIED BY PARENTS, NO PETS ALLOWED, AND PLEASE NOTE PARKING IS LIMITED. Each unit has one off street covered parking spot.

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$214.48

/ Nightly

Condo

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

Siesta Key, Florida, United States

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!

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Bath

Sleeps

$218.93

/ Nightly

Condo

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

Siesta Key, Florida, United States

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!

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Bath

Sleeps

$269.93

/ Nightly

Condo

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

Siesta Key, Florida, United States

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.

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Sleeps

$503.51

/ Nightly

Private Vacation Home

Charming spacious 3-bedroom house walking minutes from Siesta Key Beach

Siesta Key, Florida, United States

Enjoy a soothing stay at this 3-bedroom house in Siesta Key, a very short walking distance from the beach. The bedrooms feature a king, queen, and twin bed, ensuring a perfect night's sleep for all guests. With amenities like AC, WiFi, and a washing machine, your stay will be stress-free. The two bathrooms offer showers and hair dryers for added convenience. Relax in the peaceful living room with an extra queen bed.brWe look forward to welcoming you to our place.

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Sleeps

$208.14

/ Nightly

Condo

Renovated condo with easy beach access on Siesta

Siesta Key, Florida, United States

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.

2

Bed

1

Bath

4

Sleeps

$336.62

/ Nightly

Condo

Gulf Holiday-E701- Resort-Style amenities!

Siesta Key, Florida, United States

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!

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$456.72

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Condo

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

Siesta Key, Florida, United States

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.

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$396.02

/ Nightly

Apartment

Living the Dream at this Beautiful 2 Bed/1 Bath Steps from Siesta Key Beach!

Siesta Key, Florida, United States

Experience the Gulf breezes 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, 2 twins in the second bedroom, and a queen sleeper sofa in the living room, accommodating up to 6 guests. This unit, located on the ground 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*No garage parking.brbrBedroom 1: KingbrBedroom 2: 2 Twin BedsbrLiving 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*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

2

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1

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6

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