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Vacation rentals in Siesta Key

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Top-rated vacation rentals in Siesta Key

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Guest favorite
A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.
Condo in Siesta Key
4.95 out of 5 average rating, 133 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels. Washer/dryer located down the hall

Top guest favorite
A spacious bedroom features a king size bed with a white bedding set and decorative pillows. Soft blue walls provide a calming backdrop. A ceiling fan is installed overhead, and natural light streams in through the window adorned with light blinds. Complementary artwork adds a touch of coastal charm.
Guesthouse in Sarasota
4.92 out of 5 average rating, 118 reviews

Super Clean Cozy and Quaint steps from the beach

The best of all worlds, cleanliness and steps from the beach. Avoid the crowds at the public beach in this beautiful private beach with lounge chairs already at the beach for your convenience. Literally yards from the beach, exit the ground floor condo and walk 100 yards to the gate to the private beach. Only 2 miles from the village, with an easy close by trolley stop just outside the complex. Beach cart, umbrella, cooler, beach toys and towels provided for your convenience! Look no further.

Top guest favorite
A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.
Condo in Siesta Key
4.93 out of 5 average rating, 120 reviews

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

Top guest favorite
A covered patio space is surrounded by lush greenery and decorative plants. A light-colored table and two chairs are arranged on a tiled floor. Large, double doors in a vibrant blue lead to the outdoors, enhancing the welcoming atmosphere.
Guest suite in Sarasota
4.99 out of 5 average rating, 198 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Top guest favorite
A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.
Home in Sarasota
5 out of 5 average rating, 106 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

Guest favorite
The enclosed Lanai features large bay windows showcasing views of the Gulf of Mexico. A seating area includes wicker chairs and a coffee table. Light-colored walls are contrasted by wooden accents and a ceiling fan, creating a bright and airy atmosphere.
Apartment in Siesta Key
4.93 out of 5 average rating, 118 reviews

Siesta Premier Location - The 'Calm of Siesta'

My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

Top guest favorite
A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.
Condo in Siesta Key
5 out of 5 average rating, 129 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

Top guest favorite
Condo in Longboat Key
4.98 out of 5 average rating, 212 reviews

Oceanview: Open Saturday, $225/nt + Fees!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Top guest favorite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Condo in Siesta Key
4.97 out of 5 average rating, 344 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

Guest favorite
A well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.
Condo in Siesta Key
4.96 out of 5 average rating, 112 reviews

Palm Bay Club! Resort Style Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Top guest favorite
A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.
Guesthouse in Bradenton Beach
4.99 out of 5 average rating, 192 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Guest favorite
A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.
Condo in Siesta Key
4.92 out of 5 average rating, 116 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

Popular amenities for Siesta Key vacation rentals

Self check-in
Beachfront
Free parking on premises
Monthly stays
Gym

Siesta Key beach vacation rentals

Superhost
A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.
Condo in Siesta Key
4.93 out of 5 average rating, 108 reviews

The Honeymoon Suite on Siesta Key Beach

Guest favorite
A living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.
Condo in Siesta Key
4.84 out of 5 average rating, 251 reviews

Cozy 1BR Beach Condo on Siesta Key!

Guest favorite
A detailed map highlights the location of Siesta Key, showcasing nearby points of interest and roadways. The Gulf of Mexico is indicated to the southwest, while the surrounding areas and other keys are marked, providing context for travel and exploration.
Condo in Siesta Key
4.87 out of 5 average rating, 104 reviews

Bayside Sunrise Cottage on Siesta Key!

Superhost
A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.
Condo in Siesta Key
4.82 out of 5 average rating, 137 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Guest favorite
A cozy porch area features a hanging swing adorned with colorful cushions, complemented by a small dining table and chairs. The entrance is framed by green lattice work, creating a welcoming space. A sign with the text 'WELCOME' is mounted on the wall.
Cottage in Siesta Key
4.86 out of 5 average rating, 174 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Top guest favorite
Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.
Apartment in Longboat Key
4.96 out of 5 average rating, 113 reviews

Longboat Key-OCEAN FRONT- on the beach

Superhost
A beachfront pool area is shown under a bright sky, featuring palm trees and umbrellas around the pool. Guests are seen enjoying the water, with lounge chairs and colorful towels placed around the poolside. The ocean is visible in the background, completing the serene atmosphere.
Condo in Siesta Key
4.87 out of 5 average rating, 136 reviews

Private Beach Siesta Key Resort Jamaica Royale

Guest favorite
A living room area features large sliding glass doors that open to a private balcony with views of the Gulf of Mexico. Soft gray furniture is arranged around a coffee table, and a flat-screen TV is located on a media console. Natural light fills the space.
Condo in Longboat Key
4.88 out of 5 average rating, 117 reviews

Sunset and beach view from your balcony Unit 403

Siesta Key home rentals

Guest favorite
A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.
Home in Sarasota
4.93 out of 5 average rating, 106 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

Top guest favorite
A heated pool with a curved shape is surrounded by a screened patio, featuring lounge chairs positioned for relaxation. A spacious covered area showcases seating and dining options, with views of lush greenery and wooden fencing providing privacy.
Home in Sarasota
4.97 out of 5 average rating, 254 reviews

Your private retreat near Siesta Key Beach.

Guest favorite
A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.
Home in Sarasota
4.93 out of 5 average rating, 106 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Top guest favorite
A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.
Home in Sarasota
4.94 out of 5 average rating, 126 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Guest favorite
A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.
Home in Sarasota
4.84 out of 5 average rating, 279 reviews

Private Siesta Beach House Oasis with Heated Pool.

Guest favorite
A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.
Home in Sarasota
4.97 out of 5 average rating, 104 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

Top guest favorite
A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.
Home in Siesta Key
4.91 out of 5 average rating, 119 reviews

Siesta Key, FL - Casa Berano

Top guest favorite
An expansive backyard features a private heated pool, surrounded by lounge seating and a well-maintained putting green. Softly glowing twilight casts a warm hue over the space, framed by lush greenery and a serene atmosphere.
Home in Bellevue Terrace
5 out of 5 average rating, 116 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

Family friendly vacation rentals in Siesta Key

Top guest favorite
A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.
Guesthouse in Sarasota
4.99 out of 5 average rating, 238 reviews

Magical Guesthouse 1 mi from SRQ airport

Top guest favorite
Home in Arlington Park
4.95 out of 5 average rating, 19 reviews

Coastal Luxe, SaltPool/Spa, 5miles to Siesta

Top guest favorite
The studio apartment features a spacious bed with light-colored linens, complemented by two decorative pillows. A sleek brown sofa is positioned in front, adorned with a soft throw blanket. Natural light enters through the window, enhancing the clean and modern design.
Home in Sarasota
4.81 out of 5 average rating, 194 reviews

Comfortable + Functional Private Studio Apartment

Guest favorite
A quaint guest house is depicted, featuring a light-colored exterior and dual doors with windows. Surrounding greenery includes tropical plants and trees, while a wooden pathway leads to the entrance. The blue sky above complements the inviting outdoor space.
Place to stay in Sarasota
4.85 out of 5 average rating, 124 reviews

Tiny Shack in the Back

Top guest favorite
The interior of the cottage features wooden walls and a spacious layout. A comfy sofa is positioned next to a well-equipped mini kitchen, which includes cabinets and countertop space. Large windows allow natural light to fill the space, complementing the warm wood tones.
Guesthouse in Osprey
4.99 out of 5 average rating, 342 reviews

Cozy Cottage by the Bay

Top guest favorite
Guest suite in Sarasota
4.9 out of 5 average rating, 347 reviews

Siesta Keys stylish and affordable Airbnb.

Guest favorite
A red car is parked in a driveway leading to a single-story house. A garage door is visible, and the surrounding area features green grass and a wooden fence. Clear blue skies can be seen above, indicating a bright day.
Condo in Sarasota
4.75 out of 5 average rating, 395 reviews

COMFY STUDIO

Guest favorite
An aerial view showcases a private island surrounded by water, featuring lush greenery and two tiny homes. A manicured lawn is visible with seating areas, umbrellas, and pathways that create a serene outdoor environment.
Tiny home in Sarasota
4.87 out of 5 average rating, 237 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

When is the best time to visit Siesta Key?

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Avg. price€ 229€ 293€ 317€ 273€ 221€ 220€ 219€ 198€ 178€ 174€ 189€ 207
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Frequently Asked Questions

  • How is the weather in Siesta Key?

    Siesta Key enjoys a tropical climate with warm weather throughout the year. Summer temperatures can rise up to 90°F (32°C) while winter temperatures rarely drop below 50°F (10°C). The island gets a significant amount of rainfall, especially during the summer months.

  • What are some of the best things to do in Siesta Key?

    Activities in Siesta Key often revolve around its beautiful beaches, where you can swim, sunbathe, or play beach volleyball. You can also explore the local shops and restaurants in Siesta Village, or take a boat tour to spot dolphins.

  • What is the best time of year to visit Siesta Key?

    The most popular time to visit Siesta Key is during the winter and spring months when the weather is warm and comfortable. A notable local event is the Siesta Key Crystal Classic, an international sand sculpting festival that takes place every November.

  • What are the best places to stay in Siesta Key?

    Popular areas to stay in Siesta Key include Siesta Village for its proximity to dining and shopping, Crescent Beach for its quiet atmosphere, and Turtle Beach for its family-friendly environment.

  • What are the best places to visit in Siesta Key?

    Siesta Key is known for its stunning beaches such as Siesta Beach and Turtle Beach. You might also find exploring the Siesta Key Village and Point of Rocks interesting. The latter is a limestone formation on Crescent Beach attracting snorkeling enthusiasts.

  • What are some hiking trails in Siesta Key?

    While Siesta Key is more known for its beautiful beaches, you can still explore walking trails such as the Palmer Point Beach trail or Turtle beach trail. These paths provide an opportunity to enjoy the island's natural beauty and spot local wildlife.

  • What are some family activities to do in Siesta Key?

    Families can have fun exploring the Siesta Key beaches, perfect for swimming and building sandcastles. The Siesta Key Water Sports provide opportunities to engage in safe marine activities. For nature lovers, the Siesta Key Marina has dolphin watching tours.

  • What are some of the best day trip ideas in Siesta Key?

    Popular day trips from Siesta Key include visiting the vibrant city of Sarasota, which has a lively arts scene, or exploring the Myakka River State Park, known for its diverse wildlife and hiking trails.

  • Are there vacation rentals with a dedicated workspace in Siesta Key?

    Yes! Work meets play with ease at over 950 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Siesta Key?

    Four-legged friends are welcome in Siesta Key. Choose from more than 360 vacation rentals for guests traveling with pets.

  • Are there Siesta Key vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 1,570 vacation homes with pools in Siesta Key, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in cottage rentals in Siesta Key?

    Experience the best of Siesta Key with our cottage rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Siesta Key have a gym?

    Absolutely! We offer over 40 apartment rentals with a gym in Siesta Key. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Siesta Key have free parking?

    Absolutely! We offer over 20 cottage rentals with free parking in Siesta Key. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Siesta Key have a bbq area?

    Absolutely! We offer over 10 cottage rentals with a bbq area in Siesta Key. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Siesta Key have self check-in?

    Absolutely! We offer over 10 villa rentals with self check-in in Siesta Key. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly townhouse rentals in Siesta Key?

    Siesta Key has more than 70 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Siesta Key?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a gym, over 140 homes with self check-in, over 430 homes with free parking, over 190 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

All about Siesta Key

Siesta Key is an eight-mile-long barrier island off the coast of Sarasota, known for its soft quartz beaches, turquoise waters, and abundance of marine life. Due to its location on the western Florida shoreline in the balmy waters of the Gulf of Mexico, the island experiences ideal conditions year-round for swimming, paddling, and watersports. This small coastal community offers a host of recreational opportunities outside of the beach as well. Wander the Siesta Key Village, where you can find the many live music venues, boutique art shops, and souvenir vendors scattered throughout the small but lively downtown area. Check out one of the weekly farmer’s markets, spend an afternoon picking through the gift shops, or just lounge one the one of the white-sand beaches waiting for the sun to set over the Gulf.

What are the top things to do in Siesta Key?

Point of Rocks

One of the best snorkeling sites on Siesta Key, this limestone rock outcropping is home to abundant marine life and migratory bird populations. Calm waters and clear conditions make this a perfect place for beginners and experienced snorkelers alike. Expect to see schools of tropical fish, crabs, ocean sponges, and manatees during the summer. You may even get lucky and spot some of the area’s resident dolphins.

Siesta Key Drum Circle

The Siesta Key drum circle is a weekly tradition held on Sundays at Englewood and Siesta beaches throughout the year. Beginning about an hour before sunset, local artists and dancers kick off an evening of music and dancing. Large crowds gather to watch the festivities as onlookers are encouraged to dance or grab a drum and beat along.

Deep-sea fishing

Sandwiched between the vast Gulf of Mexico and Roberts Bay, Siesta Key is a year-round fishing destination. The reefs attract cobia and grouper, and if you venture further out you’ll be rewarded with tuna and wahoo. July is peak season for red snapper, while the fall bait migration off the Florida coast is a big draw for anglers from October onward.

Quick stats about vacation rentals in Siesta Key

  • Total vacation rentals

    Explore 2,020 vacation rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key vacation rentals start at € 9 per night before taxes and fees

  • Verified guest reviews

    Over 35,910 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,600 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 390 rentals that welcome pets

  • Vacation rentals with a pool

    1,620 properties feature pools

  • Rentals with dedicated workspaces

    940 properties have a dedicated workspace

  • Wi-Fi availability

    2,000 of Siesta Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront, and Free parking on premises across Siesta Key rentals

  • 4.8 Average rating

    Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key