Become a host

Vacation rentals in Siesta Key

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Siesta Key

  • Total vacation rentals

    Explore 2,200 vacation rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key vacation rentals start at R 987 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 40,870 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,820 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 390 rentals that welcome pets

  • Vacation rentals with a pool

    1,830 properties feature pools

  • Rentals with dedicated workspaces

    970 properties have a dedicated workspace

  • Wi-Fi availability

    2,170 of Siesta Key vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.8 Average rating

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

Top-rated vacation rentals in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Top guest favorite
A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.
Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

ValueFamilyLaundry

4.94 out of 5 average rating, 106 reviews
Top guest favorite
A three-story condominium building is shown, featuring a combination of palm trees and lush green landscaping at the forefront. Balconies are visible on each level, with a red-tiled roof adding a distinct character to the architecture.
Condo in Siesta Key

Seaside on Siesta Key Beach

Seaside on Siesta is the perfect walkable location to everything you need for a seaside getaway! Located directly across the street from Siesta Key Beach. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village, Stickney Point, or Turtle Beach First floor unit so no need to wait on elevators. The spectacular white quartz beach and crystal clear water awaits you just outside your door! Search "Seaside on Siesta Tour" on Youtube for a video tour.

LocationFamilyLaundry

4.95 out of 5 average rating, 127 reviews
Guest favorite
Condo in Siesta Key

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

ValueLocationGrill

4.79 out of 5 average rating, 110 reviews
Top guest favorite
Apartment in Siesta Key

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!

FamilyLocationKitchen

4.94 out of 5 average rating, 143 reviews
Guest favorite
The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.
Condo in Siesta Key

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

FamilyValueWalkability

4.85 out of 5 average rating, 110 reviews
Top guest favorite
Home in Sarasota

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

ValueLocationNearby

4.95 out of 5 average rating, 199 reviews
Guest favorite
A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.
Home in Sarasota

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

LocationValueDecor

4.8 out of 5 average rating, 189 reviews
Top guest favorite
A single-story tropical home is presented with a light blue exterior and a metal roof. Lush palm trees and colorful plants border the pathway leading to the entrance. An outdoor umbrella sits near the entry, enhancing the welcoming appearance of the property.
Home in Siesta Key

Siesta Key Beach & Village 2BR/2BA Steps to Beach

This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located in the heart of Siesta Key Village. You will be within a 2 minute walk to Siesta Key Beach and Siesta Village. With a beach house décor and equipped with 3 smart TVs, WIFI, cable, refrigerator, microwave, W/D, grill, beach chairs, toys for the kids, beach wagon, 1 queen bed, 2 twin beds and sleeper queen sofa. This private beach home has everything you need for a beach vacation. Local ownership.

ValueLocationQuiet

4.94 out of 5 average rating, 170 reviews
Top guest favorite
Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

FamilyLocationTV

4.92 out of 5 average rating, 172 reviews
Guest favorite
A modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.
Condo in Siesta Key

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything

A spacious and quiet 2-floor, 2 bedroom, 2.5 bathroom condo that lives like home and is close to everything Siesta Key offers. Spread out and enjoy YOUR vacation! Your condo features large rooms, comfy and modern surroundings, (2) Master Bedrooms upstairs, and you are steps away from a gorgeous heated pool that you can view from your lanai. This is the perfect condo for you and your family to relax in and simply enjoy your time in Siesta Key!

FamilyValueParking

4.88 out of 5 average rating, 179 reviews
Top guest favorite
A private outdoor patio is highlighted, featuring a round table surrounded by four chairs. A large blue umbrella provides shade, while tropical greenery adds a natural backdrop. Paved brick flooring completes the inviting outdoor space, ideal for relaxation.
Condo in Siesta Key

Steps to Beach & Siesta Key Village-Village condo

Steps from the sugary white sand of world famous Siesta Key Beach and the turquoise waters of the Gulf of Mexico. Our charming beach house is situated in a relaxing tropical setting with a private outdoor patio. It is ground level with a reserved parking space right in front of the unit. Newly renovated with tile floors, fully equipped kitchen with sleek granite counter-tops and pendant lighting, you will enjoy a warm and inviting atmosphere.

FamilyValueGetting around

4.93 out of 5 average rating, 244 reviews
Top guest favorite
A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.
Home in Sarasota

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

LocationFamilyWalkability

5.0 out of 5 average rating, 110 reviews

Popular amenities for Siesta Key vacation rentals

Self check-inFree parking on premisesBeachfrontMonthly staysGym

Stay near Siesta Key's top sights

Siesta Beach

1,617 locals recommend

Sarasota Beach

82 locals recommend

Crescent Beach

70 locals recommend

Siesta Key Beach

171 locals recommend

Siesta Key

81 locals recommend

The Beach Club

72 locals recommend

Siesta Key beach vacation rentals

Guest favorite
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

Private Beach Siesta Key Resort Jamaica Royale

LocationFamilyAir conditioning

4.86 out of 5 average rating, 154 reviews
Guest favorite
Home in Siesta Key

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

LocationValueGetting around

4.91 out of 5 average rating, 131 reviews
Top guest favorite
A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.
Condo in Bradenton Beach

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

ValueLocationAccuracy

4.99 out of 5 average rating, 185 reviews
Top guest favorite
Condo in Longboat Key

Island Time: Open Columbus Day Weekend!

LocationValueParks

4.98 out of 5 average rating, 258 reviews
Guest favorite
Condo in Siesta Key

Beach Retreat - Jamaica Royale Unit #52

FamilyLocationAir conditioning

4.86 out of 5 average rating, 138 reviews
Guest favorite
A spacious balcony is featured, showcasing outdoor seating arrangements with a table and four black chairs, complemented by a lounge chair. The ceiling is adorned with wooden beams, and palm trees and the ocean are visible in the background, inviting a relaxed atmosphere.
Villa in Siesta Key

Penthouse Oceanview Mermaid Villa

FamilyLocationIndoor spaces

4.88 out of 5 average rating, 116 reviews
Top guest favorite
A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.
Condo in Siesta Key

Heated Pools & Spa · Private Beach + Bay Views

LocationValueSleep quality

4.97 out of 5 average rating, 137 reviews
Top guest favorite
Home in Bradenton Beach

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

FamilyValueAir conditioning

4.98 out of 5 average rating, 128 reviews

Siesta Key home rentals

Top guest favorite
The living area features a spacious sectional sofa adorned with yellow accent pillows. Light wood floors complement the bright decor, which includes large windows with sheer curtains. A modern dining area with a table and chairs is visible, along with a well-equipped kitchen showcasing stainless steel appliances.
Home in Siesta Key

[lounge like locals]walk to siesta beach +bikes

LocationFamilyLayout

4.89 out of 5 average rating, 203 reviews
Guest favorite
A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.
Home in Gulf Gate Estates

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

FamilyValueNearby

4.8 out of 5 average rating, 138 reviews
Top guest favorite
Home in Siesta Key

Heated pool & Infrared Sauna, 2 min to beach

LocationValueQuiet

4.98 out of 5 average rating, 104 reviews
Top guest favorite
A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.
Home in Gulf Gate Estates

The Key Lime Cottage 2 miles from Siesta Key Beach

FamilyValueWifi

4.96 out of 5 average rating, 281 reviews
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

Cozy Boho Bungalow Pool/Spa Downtown Sarasota

ValueLocationComfort

4.97 out of 5 average rating, 161 reviews
Guest favorite
A heated pool is enclosed within a screened area, surrounded by lush greenery and outdoor seating. The pool area features a natural stone deck, with lounge chairs positioned for sunbathing. The peaceful environment offers a private retreat for relaxation and enjoyment.
Home in Sarasota

Heated Pool - Just 1 mile to Beach! Updated/Fun!

LocationValueTV

4.92 out of 5 average rating, 124 reviews
Guest favorite
The exterior of a newly renovated home is shown, featuring a light-colored brick facade and a modern garage door. A well-maintained driveway leads to the entrance, which is accentuated by a bright orange door. Landscaping includes gravel beds and low-maintenance plants amidst partial cloud cover.
Home in Sarasota

Gorgeous renovation with pool, minutes from beach

FamilyLocationPool

4.88 out of 5 average rating, 103 reviews
Top guest favorite
A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.
Home in Sarasota

Luxury Pool Family Oasis-Siesta Key/DT 3BR/2BA

ValueFamilyComfort

4.96 out of 5 average rating, 154 reviews

Family friendly vacation rentals in Siesta Key

Guest favorite
Apartment in Siesta Key

Siesta Key Escape | 2BR + Den | Pool & Gulf Views

FamilyValueGetting around

4.86 out of 5 average rating, 223 reviews
Guest favorite
Condo in Siesta Key

The Flamingo's Nest at Sea Club II

ValueFamilyLaundry

4.94 out of 5 average rating, 157 reviews
Superhost
A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.
Condo in Siesta Key

Crystal House on Siesta Key Beach

FamilyLocationSleep quality

4.88 out of 5 average rating, 146 reviews
Top guest favorite
Bungalow in Sarasota

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

FamilyLocationComfort

5.0 out of 5 average rating, 12 reviews
Top guest favorite
Home in Sarasota

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

LocationFamilyBathroom

5.0 out of 5 average rating, 10 reviews
Top guest favorite
Home in Siesta Key

Siesta Key House, Pool & Hot Tub, 1 mile to beach

FamilyLocationOutdoor spaces

5.0 out of 5 average rating, 15 reviews
Guest favorite
Apartment in Siesta Key

Gertrude's Siesta | Oceanview, 1-min to Beach

LocationFamilyShared spaces

4.83 out of 5 average rating, 64 reviews
Top guest favorite
Home in Siesta Key

Siesta Key Village Home

FamilyLocationBathroom

5.0 out of 5 average rating, 21 reviews

When is the best time to visit Siesta Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 4,571 ZARR 5,886 ZARR 6,577 ZARR 5,212 ZARR 4,390 ZARR 4,554 ZARR 4,143 ZARR 3,749 ZARR 3,371 ZARR 3,502 ZARR 3,815 ZARR 4,423 ZAR
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Frequently Asked Questions

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

    Many guests choose accommodations near Siesta Beach or around the lively Siesta Key Village for convenient access to shops, restaurants, and the shoreline. Quiet neighborhoods near Crescent Beach are also frequently suggested for a more relaxed atmosphere.

  • What are the best things to do in Siesta Key with kids?

    Explore sandy stretches at Siesta Beach, visit playgrounds, or try family-friendly kayaking in the gentle waters. Mini golf, ice cream spots, and shell collecting are often recommended for kids around the island.

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

    Siesta Key has powder-soft beaches, water sports like paddleboarding, and vibrant local shops in Siesta Key Village. Visitors often enjoy sunset walks, live music venues, and sampling fresh seafood at local eateries.

  • How is the weather in Siesta Key?

    Siesta Key has warm, humid summers around 90°F (32°C) and mild winters near 55–75°F (13–24°C). Rain is more common from late spring through early fall, while the winter and spring months are drier and sunnier.

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

    Siesta Beach, Crescent Beach, and Turtle Beach are frequently suggested for their distinct shorelines. Siesta Key Village has lively shops, while Point of Rocks is favored for snorkeling.

  • What are some hiking trails in Siesta Key?

    Siesta Key has gentle beachside paths and coastal walking trails, especially near beaches and nature reserves. For more variety, nearby mainland parks around Sarasota add wooded trails and wildlife viewing.

  • What are some family activities we can do in Siesta Key?

    Families often explore Siesta Beach, bike along island paths, or take boat tours for dolphin spotting. Ice cream shops, playgrounds, and interactive nature programs round out popular activities for all ages.

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

    Many guests explore nearby Sarasota for its museums, gardens, and cultural sites. Wildlife reserves, marine aquariums, and historic downtown areas around the Gulf Coast can add variety to your itinerary.

  • Are there any pet friendly accommodations available in Siesta Key?

    Siesta Key has pet-friendly accommodations in different neighborhoods, with many listings offering private outdoor spaces. While local beaches have restrictions for dogs, look for homes that include easy outdoor access for your pet to enjoy the island.

  • What are some local tips for visiting Siesta Key?

    Bring a reusable water bottle, and start beach days early for easier parking and quieter sands. Locals recommend checking out sunset drum circles and trying out watersports for a memorable experience.

  • What is Siesta Key known for?

    Siesta Key is often recognized for its powdery, quartz sand beaches, especially at Siesta Beach. The area has a laid-back atmosphere, locally owned shops, and a tradition of vibrant community events.

  • What are the best hidden gems to explore in Siesta Key?

    Point of Rocks is a favorite for snorkeling near natural limestone formations, while smaller stretches like Turtle Beach are known for quieter shorelines and shell collecting. Local artists’ galleries and tucked-away cafés are also worth discovering.

  • What are the best foods to try in Siesta Key?

    Fresh Gulf shrimp, locally caught grouper sandwiches, and key lime pie are frequently suggested around Siesta Key. Many eateries feature locally sourced seafood with tropical flavors, as well as casual beachside options.

  • What should I bring for a trip to Siesta Key?

    Pack lightweight clothing, sun protection, reusable water bottles, and swimwear. Water shoes and a sand-friendly tote can help when exploring beaches, while a light sweater is useful for cooler evenings or restaurants with air conditioning.

  • What is the nightlife in Siesta Key like?

    Siesta Key’s nightlife has casual beach bars, open-air music venues, and spots for evening bites in Siesta Key Village. Expect live acoustic sets, DJ nights, and a relaxed, welcoming vibe.

  • What are the most popular events or festivals in Siesta Key?

    The Siesta Key Crystal Classic draws many visitors each fall to celebrate intricate sand sculpting. The weekly Siesta Key Drum Circle gathers people on Siesta Beach for music and dancing, and community art shows are frequently suggested by locals.

  • Are there family friendly vacation rentals in Siesta Key?

    Family-friendly rentals are common across Siesta Key, particularly near the beaches and Siesta Key Village. Listings with extra space, outdoor areas, and amenities such as pools are often emphasized for group comfort.

  • When is the best time to visit Siesta Key?

    Spring and fall are often recommended for pleasant weather, fewer crowds, and vibrant local events. These seasons have comfortable temperatures and a mix of beach days and community happenings.

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.

Destinations to explore