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Siesta Key, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Siesta Key, FL

Best Siesta Key, FL vacation rentals with a balcony

Casa Tegula | Walking Distance To Crescent Beach! - Siesta Key, FL
9.9 98 reviews

Casa Tegula | Walking Distance To Crescent Beach!

house, Siesta Key
This Siesta Key vacation home is located just a mile from Crescent Beach and Siesta Key Beach, offering easy access to the area's top attractions. The house has received excellent ratings for location, cleanliness, and overall experience from previous guests.
The 8-bedroom house comfortably accommodates large families or groups. Guests can enjoy a private pool, a game room, a barbecue grill, and a balcony with scenic views.
Coastal Breeze Siesta – Entire 4-unit Complex With Dock - Siesta Key, FL
No reviews

Coastal Breeze Siesta – Entire 4-unit Complex With Dock

house, Vamo
This 4-unit complex in Sarasota is situated approximately an 11-minute walk from Turtle Beach and 10 miles from Marina Jack Restaurant And Marina.
This entire complex offers a private dock, a fully equipped kitchen with a dishwasher, and air conditioning for up to 31 guests.
Tropical Breeze Resort - Siesta Key, FL
No reviews

Tropical Breeze Resort

resort, Siesta Key
Tropical Breeze Resort is located on Siesta Key, just a short 3km drive from the town center, offering easy access to the famous Siesta Key Public Beach and Irma Beach. The resort is a great choice for families and couples looking for a relaxing beach vacation.
The resort has a swimming pool, a garden, and a terrace, providing ample space for relaxation and outdoor activities. Guests can also enjoy free Wi-Fi, on-site parking, and pet-friendly accommodations.
Canalfront 3/3 Townhome Siesta Key  - Walk To The Beach! - Siesta Key, FL
10 1 review

Canalfront 3/3 Townhome Siesta Key - Walk To The Beach!

apartment, Siesta Key
This Siesta Key waterfront home offers stunning views and easy beach access, located within a 10-minute walk of Siesta Key Beach and St. Boniface Episcopal Church Labyrinth, and 2 miles from Crescent Beach.
This 1830-square-foot vacation rental boasts three bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, hot tub, BBQ grills, and free WiFi.

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.

Tropical Siesta Key Villa W/ Private Patio & Pool Access In Polynesian Gardens - Siesta Key, FL
10 2 reviews

Tropical Siesta Key Villa W/ Private Patio & Pool Access In Polynesian Gardens

apartment, Siesta Key
This Siesta Key villa, located in the Polynesian Gardens neighborhood, is a half-mile walk from Siesta Key Beach Access #10 and minutes from Siesta Key Village.
The three-bedroom, two-bathroom house sleeps six guests and boasts a fully stocked gourmet kitchen, private backyard patio, screened lanai, and access to a community pool and intercoastal dock.
6415 Midnight Pass #Ph8 - Siesta Key, FL
No reviews

6415 Midnight Pass #Ph8

house, Siesta Key
This Siesta Key vacation home, 6415 Midnight Pass #PH8, 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 area attractions like the John and Mable Ringling Museum of Art (11 miles away).
This 1,250-square-foot property features two bedrooms, two bathrooms, and accommodates up to 11 guests, boasting a private pool, Jacuzzi, sauna, fitness center, tennis court, and free Wi-Fi; on-site parking is also available.
70 M² Condo ∙ 1 Bedroom ∙ 4 Guests - Siesta Key, FL
10 2 reviews

70 M² Condo ∙ 1 Bedroom ∙ 4 Guests

apartment, Siesta Key
This Siesta Key condo offers a prime location near Sarasota, with easy trolley access to multiple beach access points and a short tram ride to Siesta Key Village's shops and restaurants.
The 740-square-foot unit features one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, screened lanai, covered parking, and access to a heated pool, tennis/pickleball court, and fishing pier.
Beachfront Getaway In Siesta Key - Siesta Key, FL
9.6 594 reviews

Beachfront Getaway In Siesta Key

apartment, Siesta Key
This Siesta Key apartment is just steps away from the #1 beach in the US, offering direct access to the soft, sugar-white sands of Siesta Key Beach. This rental has excellent ratings for location, cleanliness, and user experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. The apartment offers a modern kitchen, a private beachfront seating area, a heated pool, a full-size washer and dryer, and easy access to all the attractions Siesta Key has to offer.

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?

  • Where is the best place to stay in Siesta Key?

    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?

  • What are popular theme parks near Siesta Key?

    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?

  • What are the best events in Siesta Key?

    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.

Popular destinations

Best Siesta Key, FL vacation rentals with parking

Anchorage Resort Top Floor 2 Bdrm Condo - Siesta Key, FL
9.4 46 reviews

Anchorage Resort Top Floor 2 Bdrm Condo

apartment, Siesta Key
This Siesta Key rental is a short walk from Crescent Beach and Siesta Key Marina, and less than a mile from Siesta Key Beach, offering easy access to the island's prime attractions.
This 1,250-square-foot apartment features two bedrooms, two bathrooms, and accommodates up to six guests, boasting a private balcony, swimming pool, fitness center, tennis court, and free parking.
Unit 350 - 2 Bedroom 2 Bathroom Bay Side Standard Condominium - Siesta Key, FL
9.8 71 reviews

Unit 350 - 2 Bedroom 2 Bathroom Bay Side Standard Condominium

apartment, Siesta Key
This Bayside Siesta Key condo, a short walk from Siesta Key Beach and Crescent Beach, offers convenient access to Gulf-side amenities.
The 1,090-square-foot apartment features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, in-unit entertainment, a private patio, pool, hot tub, and parking.
Location! Minutes To Siesta Key Beaches. Spa Oasis. - Siesta Key, FL
10 1 review

Location! Minutes To Siesta Key Beaches. Spa Oasis.

apartment, Siesta Key
This Siesta Key vacation rental is a two-bedroom, two-bathroom apartment located a short 10-minute walk from Siesta Key Beach, offering easy access to St. Armands Circle and the Mall at University Town Center.
This pet-friendly condo sleeps six, features air conditioning, internet, and boasts on-site banana, avocado, and guava trees, providing a convenient base for exploring Sarasota's attractions including Ed Smith Stadium and the Stardust Event Center.
Palm Bay Club Bayside Pools Hot Tub, Private Beach - Siesta Key, FL
9.3 169 reviews

Palm Bay Club Bayside Pools Hot Tub, Private Beach

apartment, Siesta Key
This beachfront apartment is conveniently located on Siesta Key, just a short walk from Siesta Key Beach and Crescent Beach, offering easy access to the area's most popular attractions. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom apartment is spacious and comfortably accommodates up to six people, providing ample room for families or groups of friends. Guests can enjoy a variety of amenities, including a swimming pool, spa, fitness center, and tennis court, as well as a fully equipped kitchen, free Wi-Fi, and a private terrace.

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.

Anchorage Resort 3rd Floor 2 Bedroom Condo+ Beach - Siesta Key, FL
8.8 72 reviews

Anchorage Resort 3rd Floor 2 Bedroom Condo+ Beach

apartment, Siesta Key
This Siesta Key apartment is conveniently located within a 10-minute walk of Siesta Key Marina and Crescent Beach, and just 0.6 miles from Siesta Key Beach. Guests have consistently rated this rental "very good" for cleanliness and "excellent" for location.
The 1250-square-foot apartment comfortably accommodates up to 6 guests with 2 bedrooms. Amenities include a fully equipped kitchen, a balcony, air conditioning, a swimming pool, a jacuzzi, and parking.
Charming Siesta Key Condo With Private Beach Access - Siesta Key, FL
9.5 4 reviews

Charming Siesta Key Condo With Private Beach Access

house, Siesta Key
This Siesta Key condo, a six-minute walk from Crescent Beach and eleven miles from the John and Mable Ringling Museum of Art, offers convenient access to Siesta Key's attractions. This 960-square-foot unit features one bedroom, one bathroom, sleeps seven guests, and includes a private beach access, swimming pool, sauna, fitness center, and tennis court.
Gulf Views, Roof Top Deck, And Game Room! - Siesta Key, FL
9.6 68 reviews

Gulf Views, Roof Top Deck, And Game Room!

apartment, Siesta Key
This Siesta Key vacation rental is located just a mile from Siesta Key Beach and St. Boniface Episcopal Church Labyrinth, offering easy access to the area's top attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 3-bedroom home spans 2,600 square feet and includes a private pool, a balcony, a garden, a spa, a restaurant, and a water park. You'll also find amenities like a washing machine, air conditioning, and parking.
Tropical Decor That Overlooks The Pool #220 - Siesta Key, FL
8.9 26 reviews

Tropical Decor That Overlooks The Pool #220

apartment, Siesta Key
This Siesta Key apartment is conveniently located near the world-renowned Siesta Key Beach, within a mile of St. Boniface Episcopal Church Labyrinth and just over two miles from Crescent Beach and Siesta Key Marina. Guests have consistently rated the apartment "very good" for cleanliness and user experience, with an "excellent" location rating.
The 870-square-foot apartment comfortably sleeps four guests in two bedrooms and one bathroom. Amenities include a fully equipped kitchen, laundry facilities, a private lanai, and access to a swimming pool, fitness center, tennis court, and parking.

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.

Shore Enough #4 - Siesta Key, FL
9.4 23 reviews

Shore Enough #4

apartment, Siesta Key
Minutes To Siesta Or Dt W/heated Pool And Hot Tub - Siesta Key, FL
9.8 120 reviews

Minutes To Siesta Or Dt W/heated Pool And Hot Tub

apartment, Siesta Key
On Siesta Key Beach - No Streets To Cross! Large, Heated Pool. - Siesta Key, FL
8.8 9 reviews

On Siesta Key Beach - No Streets To Cross! Large, Heated Pool.

apartment, Siesta Key
Charming 2br, 2ba Condo In Palm Bay Club, Sarasota - Perfect Getaway For 4! - Siesta Key, FL
9.0 33 reviews

Charming 2br, 2ba Condo In Palm Bay Club, Sarasota - Perfect Getaway For 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.

Pink Mango Cottage Steps From The Beach - Siesta Key, FL
10 16 reviews

Pink Mango Cottage Steps From The Beach

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.

5 Minutes To Private Siesta Key Beach + 2 Pools - Siesta Key, FL
9.8 180 reviews

5 Minutes To Private Siesta Key Beach + 2 Pools

apartment, Siesta Key
Peaceful Siesta Key Condo - Short Stroll To #1 Beach - Siesta Key, FL
10 1 review

Peaceful Siesta Key Condo - Short Stroll To #1 Beach

house, Siesta Key
2nd Floor Lakeview Condo In Siesta Key With Private Beach Access - Siesta Key, FL
10 1 review

2nd Floor Lakeview Condo In Siesta Key With Private Beach Access

house, Siesta Key
Siesta Key - 2br - Beachfront Condo On Crescent Beach - Heated Pool - Tennis Ct - Siesta Key, FL
10 65 reviews

Siesta Key - 2br - Beachfront Condo On Crescent Beach - Heated Pool - Tennis Ct

apartment, Siesta Key
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