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Best Vacation rentals and Airbnb offers in Siesta Key, FL
8.6 235 reviews
Siesta Key, FL
06/18 – 06/26
$307/nighttotal: $2456 (8 )
Fanta-sea 55 By Beachside Management
1 4
house , Siesta Key
This Siesta Key vacation home sits just steps from the famous white sand beach and a short drive from Crescent Beach. Guests rave about the excellent location, cleanliness, and overall experience. The house has four bedrooms and one bathroom, comfortably accommodating a family or group of friends. Enjoy the private beach access, swimming pool, spa, and tennis court, along with the fully equipped kitchen, outdoor dining area, and free parking.
9.9 73 reviews
Siesta Key, FL
08/22 – 09/05
$203/nighttotal: $2842 (14 )
Siesta Key Spacious, Modern 2 Bed, 2 Bath Condo
1 3
apartment , Siesta Key
This Siesta Key condo is conveniently located just steps from the heated swimming pool and less than a 10-minute walk to two beach accesses, making it perfect for enjoying the island's main attractions. This rental has received excellent ratings for location, cleanliness, and overall user experience. The two-bedroom, two-bathroom apartment comfortably sleeps six guests and features a fully equipped kitchen, beach chairs, umbrellas, and a locker for storing your beach essentials. Relax in the jacuzzi tub, watch cable TV, or enjoy the BBQ area, clubhouse, and shuffleboard on the premises.
9.0 179 reviews
Siesta Key, FL
07/04 – 07/07
$658/nighttotal: $1974 (3 )
Canal 313 - Right In Siesta Key Village!
2 1
house , Siesta Key
This Siesta Key Village rental home is located a short distance from Siesta Key Beach and 1.3 miles from Crescent Beach, offering easy access to Siesta Key's renowned beaches and approximately 10 miles from the Ringling Museum of Art and Sarasota Bradenton International Airport. This 1000-square-foot vacation home features two bedrooms and two bathrooms, a private pool, tennis court, free Wi-Fi, and a fully equipped kitchen, comfortably accommodating families or small groups.
9.4 7 reviews
Siesta Key, FL
07/08 – 07/14
$294/nighttotal: $1764 (6 )
2br Siesta Key Condo - Beach Access - Gbb 1340
2 4
apartment , Siesta Key
This recently updated two-bedroom, two-bathroom condo is located in the Gulf and Bay - Bayside complex on Siesta Key, offering private beach access and proximity to Siesta Key's restaurants and shops. The second-floor unit features a bright, open layout with new furniture, a modern kitchen with granite countertops, a private lanai, and access to two heated pools, tennis courts, and pickleball courts; it comfortably sleeps five guests.
9.5 157 reviews
Siesta Key, FL
07/10 – 07/12
$425/nighttotal: $850 (2 )
Siesta Cooler: Only Minutes Walk To Siesta Beach!
1 2
apartment , Siesta Key
This Siesta Key apartment is just a short walk from the famous Siesta Key Beach, making it ideal for enjoying the sun, sand, and water. Guests consistently rate the location, cleanliness, and overall experience as excellent. This one-bedroom unit offers 800 square feet of comfortable living space. Enjoy amenities like a private balcony, a well-equipped kitchen, a swimming pool, a tennis court, and free Wi-Fi.
9.3 84 reviews
Siesta Key, FL
07/16 – 07/19
$362/nighttotal: $1086 (3 )
Luxury Waterfront Views - Heated Pool - 1400sf Duplex - Minutes To The Beach
2 2
apartment , Siesta Key
This Siesta Key duplex, a 4-minute walk from Crescent Beach and 1.2 miles from Siesta Key Beach, offers convenient access to Sarasota's attractions. The 1400-square-foot, two-bedroom, three-bathroom unit features a private heated pool, on-site tennis courts, and a fully equipped kitchen, perfect for families or groups.
10 134 reviews
Siesta Key, FL
01/01 – 03/31
$287/nighttotal: $25543 (89 )
Siesta Key Couple's Get Away!!!
1 2
apartment , Siesta Key
This Siesta Key condo rental is conveniently located within one mile of Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offering easy access to pristine sands and various water activities. The one-bedroom, one-bathroom apartment sleeps two guests and features a fully equipped kitchen with a refrigerator, oven, stovetop, and microwave, plus a swimming pool, and is part of a smoke-free building.
Siesta Key, FL
06/23 – 06/30
$170/nighttotal: $1190 (7 )
80 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests
2 2
apartment , Siesta Key
This 3rd-floor walk-up condo offers prime Siesta Key access, putting you within a 5-minute walk to Siesta Beach and close to local shops and restaurants. This 860 sq ft condo sleeps up to 6 guests and features a fully equipped kitchen, private balcony, air conditioning, and access to resort-style amenities including multiple swimming pools, tennis courts, and a workout facility.
10 64 reviews
Siesta Key, FL
10/31 – 11/07
$351/nighttotal: $2457 (7 )
Siesta Key - 2br - Beachfront Condo On Crescent Beach - Heated Pool - Tennis Ct
2 4
apartment , Siesta Key
This Siesta Key apartment is conveniently located within a 15-minute walk of Crescent Beach and Siesta Key Beach, and within 1 mile of the marina and Point of Rocks. The apartment boasts excellent user, location, and cleanliness ratings. This 2-bedroom, 2-bathroom vacation rental comfortably accommodates up to 6 guests. The apartment offers a fully equipped kitchen, a private balcony, and access to a swimming pool, a sauna, a spa, and a garden.
9.6 346 reviews
Siesta Key, FL
07/01 – 07/04
$404/nighttotal: $1212 (3 )
Steps To Siesta Beach, Chic Studio, Pool & Patio
1 2
studio , Siesta Key
This Siesta Key apartment is located just a short walk from the beach, putting you right in the heart of the action. Reviewers consistently rate it excellent for location, cleanliness, and overall experience. The 580-square-foot apartment comfortably accommodates four guests in one bedroom and one bathroom. Enjoy a private pool, outdoor amenities, and a fully equipped kitchen, perfect for a relaxing beach getaway.
Best Siesta Key, FL vacation rentals with a balcony
9.0 11 reviews
Siesta Key, FL
07/04 – 07/07
$648/nighttotal: $1944 (3 )
New Listing! Pool Jacuzzi, 3-min To Beach Bars & Entertainment!
2 1
house , Siesta Key
This Siesta Key vacation rental is a one-minute walk from Crescent Beach and a short drive from Turtle Beach, providing easy access to Siesta Key's attractions. This 900-square-foot house features two bedrooms, two bathrooms, accommodates up to 15 guests, and includes a private pool, jacuzzi, and fully equipped kitchen with a dishwasher and microwave.
Siesta Key, FL
06/26 – 06/27
$1949/nightfor 1 night
Bimini Breeze | Steps To Beach & Village
2 2
apartment , Siesta Key
This 2-bedroom, 2-bathroom condo in Siesta Key Village offers unparalleled walkability, just a 5-minute walk from Siesta Key Beach and a 3-minute walk from Siesta Key Village. This dog-friendly unit accommodates up to 6 guests with a fully equipped kitchen, private resort-style pool, outdoor dining area, and included beach essentials.
Siesta Key, FL
06/19 – 06/21
$1365/nighttotal: $2730 (2 )
New! Key Life Cove | Entire Duplex Near Crescent Beach With Private Outdoor Living
4 6
apartment , Siesta Key
This duplex in Siesta Key offers two private, renovated units ideal for group stays, situated a 5-minute walk from Point of Rocks Beach and a quick drive to Crescent Beach, with convenient access to South Village and Siesta Key Village. This 2280 sq ft accommodation sleeps 8 guests across 4 bedrooms and 4 bathrooms, featuring individual living spaces, private fenced backyards with outdoor dining and grills, vintage video game tables, complimentary WiFi, and easy access to the Siesta Key Trolley.
9.6 89 reviews
Siesta Key, FL
10/03 – 10/31
$188/nighttotal: $5264 (28 )
Harbor Towers 3rd Floor, Bay Views
1 2
house , Siesta Key
Harbor Towers 1 Bedroom Pool View is located in Siesta Key, just a short walk from Crescent Beach and less than a mile from Siesta Key Beach, offering easy access to the area's most popular attractions. This rental has earned excellent ratings for location, cleanliness, and user experience. This comfortable vacation rental features a modern kitchen, a private balcony, and a swimming pool. Guests can enjoy a variety of amenities, including free Wi-Fi, a fitness center, a tennis court, and on-site parking.
Where to stay in Siesta Key?
Siesta Key Village
Siesta Beach is renowned for its crystal-clear waters and powdery white sand, which attract tourists from all over the United States. Furthermore, the beach hosts an annual sand sculpture competition that draws talented artists from across the globe, where they engage in a friendly rivalry to create masterpieces out of sand.
Crescent Beach
Crescent Beach is a quieter and less crowded beach than Siesta Beach, with a family friendly atmosphere. It has a coral reef called Point of Rocks, which is a popular site for diving and snorkeling, where tourists often go in search of treasures and shipwrecks because according to the legend of the sector, the Spanish pirate José Gaspar used to hide in this area to plan his raids.
Siesta Beach
Siesta Key Village is a seaside neighborhood has a lively and festive atmosphere, especially at night, for hosting the "Siesta Key Drum Circle," a weekly event where local musicians gather to play live music and dance on the beach at sunset.
Turtle Beach
Turtle Beach is a place where sea turtles lay their eggs. Visitors can have the opportunity to witness the exciting moment and months later when the hatchlings make their way to the ocean. It is a unique and fascinating spectacle for marine life lovers.
Our Favorite Family-Friendly Vacation Rentals in Siesta Key, FL
Find the perfect family vacation rental or Airbnb in Siesta Key, FL with plenty of room to spread out near local beaches.
Siesta Key, FL
07/05 – 07/12
$392/nighttotal: $2744 (7 )
6415 Midnight Pass #210
2 5
house , Siesta Key
This Siesta Key vacation rental, 6415 Midnight Pass #210, is a 7-minute walk from Crescent Beach, 1.6 miles from Turtle Beach, and 1.8 miles from Siesta Key Beach, offering convenient access to popular attractions. This 1,250-square-foot property boasts two bedrooms, two bathrooms, and accommodates up to 11 guests, featuring a private pool, jacuzzi, sauna, fitness center, tennis court, and free Wi-Fi.
9.8 336 reviews
Siesta Key, FL
07/06 – 07/10
$276/nighttotal: $1104 (4 )
Cottage On Siesta Key Beach
1 3
apartment , Siesta Key
This Siesta Key cottage is located in a quiet residential area, just steps from the famous Siesta Key Beach and a short walk from the Point of Rocks. It has excellent ratings for location, cleanliness, and user experience. The cottage has 2 bedrooms and 2 bathrooms, comfortably sleeping 5 guests. Amenities include a private beach entrance, a shared pool, a fishing dock, a boat dock, a Tiki Hut with grills, and two private parking spots.
10 33 reviews
Siesta Key, FL
07/09 – 07/11
$2439/nighttotal: $4878 (2 )
Serenity Cottage | Multilevel Home On Siesta Key W/ Private Pool & Spa, Short Walk To Beach!
3 4
apartment , Siesta Key
This Siesta Key vacation home is located just a short walk from Point of Rocks and Crescent Beach, offering easy access to the beautiful coastline. Guests consistently rate this property as excellent, making it a popular choice for Siesta Key travelers. The home features 3 bedrooms and 4 bathrooms, comfortably accommodating up to 8 guests in its 2,060 square feet of space. Enjoy amenities like a private pool, a spacious balcony, a fully equipped kitchen, and free WiFi, making this home ideal for both relaxation and exploring all that Siesta Key has to offer.
9.8 131 reviews
Siesta Key, FL
06/17 – 06/26
$165/nighttotal: $1485 (9 )
Quiet Sarasota Charm Near Memorial Hospital & Siesta Key
2 6
apartment , Sarasota
This Sarasota home is conveniently located near shopping, beaches, and downtown, making it easy to explore all that the city has to offer. Guests consistently rate the property excellent for its location, cleanliness, and overall experience. The 1300-square-foot home comfortably accommodates up to 6 guests with two bedrooms and two bathrooms. Enjoy a private, fenced-in yard, a fully-stocked kitchen, beach essentials, and a relaxing outdoor space with a barbecue, table, and chairs.
Frequently Asked Questions about vacation rentals in Siesta Key, FL
What are some interesting places to visit in or near Siesta Key, FL?
Siesta Key is known for its beautiful beaches, but there are also some great places to visit nearby. You can check out the Siesta Key Drum Circle, a local tradition that happens every Sunday evening. For something a little more historical, head to the Marie Selby Botanical Gardens in Sarasota, just a short drive away. If you're looking for some shopping and dining, the charming downtown area of Sarasota is also worth a visit.
What are the best Airbnb and vacation rentals in Siesta Key, FL?
What types of vacation rentals are available in Siesta Key?
When you are planning a holiday in Florida you want to look for the best vacation rentals in Siesta Key. This would allow you to make the most of your holidays and get the best accommodation experiences. Vacation rentals are a good option for those who prefer privacy and comfort. Hence, you can look for various vacation rentals like apartments, condos, lofts, and townhouses for a great holiday stay. These apartments and condos come in different sizes and therefore you can decide from small studio apartments to large townhouses that have multiple rooms and additional kitchen and lounge areas.
Which walking or cycling routes are the best in Siesta Key, FL?
The Siesta Key Beach Walk is a popular choice for both walking and cycling, offering stunning views of the Gulf of Mexico. If you're looking for a more challenging ride, the Legacy Trail is a great option, connecting Siesta Key to Sarasota and offering scenic views of the area. For a shorter walk, the Siesta Key Village is perfect for strolling and enjoying the shops and restaurants.
What are the most popular Airbnbs in Siesta Key, FL?
What are the unmissable activities to do in Siesta Key?
1. Spend a Day at Siesta Key Beach - If you are in Siesta Key you need to explore the beach and spend a day here relaxing or playing volleyball or just watching the people pass by. 2. Stroll the Siesta Key Village - When you are done with the beach you can put on those walking flip-flops and head to Siesta Key Village where you can enjoy the best meals at a local restaurant and sip cold beers. 3. Buy at Farmers Market - If you love to shop you would want to visit the Farmers Market which is a great way to buy local produce and interact with the local farmers.
What sports or outdoor activites can visitors enjoy in and around Siesta Key, FL?
Siesta Key is a paradise for outdoor enthusiasts. You can enjoy swimming, sunbathing, kayaking, paddleboarding, and fishing right on the beach. For a more adventurous experience, try parasailing or jet skiing. If you're looking for something a little more relaxing, you can go for a bike ride or take a walk through the Siesta Key Beach Park.
What are the best vacation rentals with a pool in Siesta Key, FL?
If you are visiting Siesta Key for the first time you would want to look for the best accommodations in Siesta Key Village. This is the downtown area of the island and this is where most of the action happens. Hence, you can find plenty of rental properties and even hotels located here. Also, when you are planning to stay in Siesta Key you want better accessibility to other areas like Sarasota and therefore you would want to look for Siesta Key Village accommodations. You can also have access to some of the best restaurants, bars, clubs and breweries here.
What other towns or cities can be easily accessed from Siesta Key, FL?
Siesta Key is conveniently located near several other towns and cities. You can easily drive to Sarasota, which is about a 10-minute drive, and offers a variety of attractions, including museums, theaters, and restaurants. You can also visit the charming town of Venice, known for its beautiful beaches and historic downtown area, which is about a 30-minute drive. For a day trip, consider heading to St. Petersburg, about an hour away, which is home to the Dali Museum and the vibrant waterfront.
What are the best rentals for families and kids in Siesta Key, FL?
1. Big Rock Amusements LLC - 30 minutes south of Siesta Key you can find Big Rock Amusement LLC where you can take your child for some thrilling rides and games and activities to keep them busy throughout the day. 2. Jumpin Fun Inflata Park - Located in Sarasota, Jumpin Fun Inflata Park is a great space where you can take your child for some inflatable theme park games. This is where kids can enjoy jumping activities and indoor activities. 3. Sky Zone Trampoline Park - Trampoline activities are fun and therefore you can look for Sky Zone Trampoline Park in Sarasota where you can let your child enjoy freestyle bouncing and do other activities.
What amenities are commonly available in vacation rentals in Siesta Key, FL?
Vacation rentals in Siesta Key offer a wide range of amenities to make your stay comfortable. Most rentals include a fully equipped kitchen, private bathrooms, and laundry facilities. Many also feature private pools, hot tubs, and balconies or patios. Some rentals even offer additional amenities like beach gear, bicycles, and kayaks.
What are the best rentals or Airbnbs with a jacuzzi in Siesta Key, FL?
1. Chalk Festival - If you are interested in chalk art you can visit the Chalk Art Festival which takes place in Sarasota and Siesta Key. Here you can witness many professional chalk artists come together for the best chalk art competition. 2. Siesta Key Chamber Golf Tournament - Golfers can participate in the Siesta Key Chamber Golf Tournament where you can register for the 18-hole golf course and enjoy this champion-style event. 3. Siesta Key Crystal Classic International Sand Sculpting Festival - If you are visiting Siesta Key in November you can visit the Siesta Key Beach for the sand sculpting festival that takes place here.
What time of year is best to rent a vacation rental Siesta Key, FL?
The best time to visit Siesta Key is during the shoulder seasons, from April to May and September to October, when the weather is still warm but the crowds are smaller. If you're looking for the best deals, consider visiting during the off-season, from November to March, but be aware that the weather can be a bit cooler and rainier during these months.
What are the local dishes in Siesta Key, FL region?
The Siesta Key area is known for its fresh seafood, so you'll find plenty of restaurants serving up delicious dishes like grouper sandwiches, shrimp scampi, and stone crab claws. You'll also find a variety of other cuisines, including Italian, Mexican, and Asian. For a truly local experience, try a fresh-caught grouper sandwich or a plate of stone crab claws.
Destinations nearby
Best Siesta Key, FL vacation rentals with parking
9.0 1173 reviews
Siesta Key, FL
10/04 – 10/09
$313/nighttotal: $1565 (5 )
Siesta Key 1-bedroom Condo | Unit 102b At The Beach Club Steps To The Beach
2 5
apartment , Siesta Key
The Beach Club At Siesta Key #103e Resort By Rva is a smoke-free condo building located directly on Siesta Key, within a mile of Crescent Beach and Siesta Key Beach, and within 15 minutes of Siesta Key Marina and Point of Rocks. Guests consistently rate the resort excellent for its location, cleanliness, and overall experience. The condo features two bedrooms, a sofa bed, and a fully equipped kitchen, providing ample space and comfort for families or groups. Guests can relax in the spa tub, enjoy outdoor dining with the barbecue grills, and stay connected with free WiFi, while also enjoying the convenience of a modern kitchen with a refrigerator, oven, stovetop, and microwave.
9.0 85 reviews
Siesta Key, FL
07/25 – 07/30
$285/nighttotal: $1425 (5 )
Luxury Condo Ground Floor Across The Street From The #1 Beach
2 5
apartment , Siesta Key
This ground floor condo is located directly across the street from Siesta Key's #1 ranked beach, offering easy access to the sand and surf. It has received excellent ratings from previous guests. This two-bedroom, two-bathroom apartment comfortably sleeps six guests and boasts a spacious 1000 square feet of living space. Enjoy the Florida sunshine from your private lanai, relax by the heated pool, and take advantage of the fully equipped kitchen, high-speed internet, and beach amenities.
9.5 121 reviews
Siesta Key, FL
07/10 – 07/12
$581/nighttotal: $1162 (2 )
Minorga Sand Dollar On The Key
2 2
house , Siesta Key
This house is located just an 8-minute walk from the world-famous Siesta Key Beach and a short drive from attractions like The John and Mable Ringling Museum of Art and Sarasota Opera. The house has earned excellent ratings for location, cleanliness, and user experience. The house features a comfortable seating area for enjoying beautiful views or unwinding after a day of exploring. It also offers air conditioning, free Wifi, satellite TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven.
Neighborhoods and points of interest in Siesta Key, FL
Search Vacation Rentals with Swimming Pool in Siesta Key, FL
Complement your time by the water with a dip in the pool at these Siesta Key, FL vacation rentals with on-site swimming facilities.
9.5 38 reviews
Siesta Key, FL
06/17 – 06/21
$323/nighttotal: $1292 (4 )
No Car Needed! Walk To Beach + Heated Pool Retreat
1 4
house , Siesta Key
This three-level Siesta Key townhouse is a 3-minute walk from Crescent Beach and a 10-minute drive from downtown Sarasota, offering easy access to St. Armands Circle and various attractions. The 3-bedroom, 3-bathroom house sleeps 6, features a private heated pool, screened porch, garage parking, and includes beach toys, chairs, and a cart for convenient beach access; a grill and board games are also available.
Siesta Key, FL
07/16 – 07/19
$350/nighttotal: $1050 (3 )
Gulf Holiday Unit 3 By Prime Vacations
1 2
apartment , Siesta Key
Gulf Holiday Unit 3 by Prime Vacations is located steps from Siesta Key Beach, 6.4 miles from Marina Jack Restaurant and Marina, and 10 miles from the John and Mable Ringling Museum of Art. This 410 square foot condo accommodates up to 3 guests and includes a full kitchen, air conditioning, Wi-Fi, and on-site parking.
9.5 20 reviews
Siesta Key, FL
06/17 – 06/26
$378/nighttotal: $3402 (9 )
Paradise Awaits!
2 6
apartment , Siesta Key
This Siesta Key condo rental is conveniently located less than a mile from Crescent Beach and Siesta Key Beach, and within a 10-minute drive of Siesta Key Marina and Point of Rocks. This two-bedroom, two-bathroom vacation rental sleeps six guests and boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, a private terrace, and access to a community pool, jacuzzi, and BBQ grills.
Siesta Key, FL
06/22 – 06/27
$220/nighttotal: $1100 (5 )
Siesta Harbor 2br – 55+ Pool, Hot Tub & Beach
1 2
apartment , Siesta Key
This third-floor condo in Siesta Harbor, a 55+ bayside community, offers panoramic Intracoastal Waterway views and is located just north of the Stickney Point Bridge, providing walkable access to South Village shops and dining, with deeded private beach access to Crescent Beach directly across the street. This Siesta Key apartment features 2 bedrooms, 2 bathrooms, and accommodates up to 4 guests with a fully stocked kitchen, air conditioning, a swimming pool, Jacuzzi, garden, and included beach essentials, plus community boat docks with open water and Intracoastal access.
Search Coastal Vacation Rentals near Siesta Key, FL
Discover beautiful beach towns with these seaside vacation rentals in Siesta Key, FL, perfect for relaxing near the coast and exploring the shore.
9.0 73 reviews
Siesta Key, FL
08/01 – 08/08
$320/nighttotal: $2240 (7 )
Siesta Bayside: Quiet Ground-floor Villa With Private Beach Access, Heated Pools, Tennis, & Fishing!
2 2
apartment , Siesta Key
10 14 reviews
Siesta Key, FL
07/01 – 07/04
$784/nighttotal: $2352 (3 )
Pineapple On Siesta Key
3 9
apartment , Siesta Key
10 11 reviews
Siesta Key, FL
07/05 – 07/12
$270/nighttotal: $1890 (7 )
Book Me Baby! Esquina Paraiso On Siesta Key
2 5
apartment , Siesta Key
9.4 16 reviews
Siesta Key, FL
06/17 – 06/21
$332/nighttotal: $1328 (4 )
Newly Renovated Beach-side Villa | Pool | Dock
1 4
apartment , Siesta Key
Browse Luxury Vacation Rentals in Siesta Key, FL
These high-end vacation rentals in Siesta Key, FL offer luxury living and unmatched quality near the shore.
9.6 72 reviews
Siesta Key, FL
07/13 – 07/17
$240/nighttotal: $960 (4 )
Pineapple Cove: Ground-floor Comfort; Short Walk To Beach, Dining & Shops!
1 2
apartment , Siesta Key
Choose the Right Vacation Rentals with a Steam Room in Siesta Key, FL
Maximize your wellness with vacation rentals in Siesta Key, FL featuring on-site saunas and steam rooms.