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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

The Beach Club At Siesta #100b - Siesta Key, FL
No reviews

The Beach Club At Siesta #100b

house, Siesta Key
This vacation home in Siesta Key's Point O'Rocks district is located steps from Crescent Beach, 11 miles from the John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 500 square feet rental accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, a private patio, a swimming pool, a hot tub, a fitness center, tennis court, and free WiFi and parking.
Coastal Condo, Water Views, Fishing Dock & 0.6 Miles To Siesta Beach - Siesta Key, FL
No reviews

Coastal Condo, Water Views, Fishing Dock & 0.6 Miles To Siesta Beach

house, Siesta Key
This Siesta Key vacation home offers a prime location, just a 4-minute walk to Crescent Beach and 3,168 feet to Siesta Beach, with the John and Mable Ringling Museum of Art and the airport both 11 miles away.
This 1,330 square foot, air-conditioned residence accommodates up to 14 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, living room, balcony, swimming pool, spa, and access to a fishing dock.
Charming 2br Bayside Condo In Sarasota, Perfect For A Family Getaway. - Siesta Key, FL
9.0 37 reviews

Charming 2br Bayside Condo In Sarasota, Perfect For A Family Getaway.

apartment, Siesta Key
This Siesta Key condo, located bayside with easy access to Siesta Key Beach and Crescent Beach, offers proximity to St. Armands Circle and the Mall at University Town Center.
This 1,090-square-foot rental boasts two bedrooms, two bathrooms, sleeps six guests, and features a fully equipped kitchen, private patio, two pools, a hot tub, and tennis courts within the complex.
Spacious 3br Siesta Key Condo With Private Beach Access - Siesta Key, FL
9.5 2 reviews

Spacious 3br Siesta Key Condo With Private Beach Access

house, Siesta Key
This 3-bedroom condo in Siesta Key offers direct private beach access and is an 8-minute walk from Crescent Beach, 7 miles from Marina Jack Restaurant And Marina and Sarasota Opera, and 11 miles from The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This air-conditioned unit spans 1800 square feet, accommodates up to 11 guests, and features a swimming pool, garden, sauna, fitness center, tennis court, and balcony with views.

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.

Beach Rd, 300ft To Beach Access & 500ft To Village - Siesta Key, FL
9.9 73 reviews

Beach Rd, 300ft To Beach Access & 500ft To Village

chalet, Siesta Key
This Siesta Key studio rental is 100 steps from Siesta Key Beach and a five-minute walk from Siesta Village, offering prime access to the area's renowned attractions.
The third-floor unit features a queen-sized bed, kitchenette with stove, fridge, and microwave, free high-speed internet, and accommodates two guests; shared amenities include grills, a washer/dryer, and an outdoor sand wash area, plus concierge services are available.
Extraordinary Bay Views - Siesta Key - Siesta Key, FL
No reviews

Extraordinary Bay Views - Siesta Key

house, Siesta Key
This Siesta Key house offers extraordinary bay views and is located 11 miles from the John and Mable Ringling Museum of Art, with Crescent Beach just an 11-minute walk away.
This 960 square foot rental accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring an outdoor swimming pool, garden, sauna, and complimentary Wi-Fi.
Siesta Beach Condo Rental With Direct Beach And Pool Access - Siesta Key, FL
9.5 2 reviews

Siesta Beach Condo Rental With Direct Beach And Pool Access

house, Siesta Key
This Siesta Key condo, an eight-minute walk from Crescent Beach and one mile from Siesta Key Beach, offers direct beach and pool access.
The 780-square-foot property boasts a two-bedroom layout, accommodating up to nine guests and featuring a fully equipped kitchen, private parking, and a shared pool.
Gertrude's Siesta | Bayview Unit W/ Balcony, Pools & Private Beach! - Siesta Key, FL
9.2 32 reviews

Gertrude's Siesta | Bayview Unit W/ Balcony, Pools & Private Beach!

apartment, Siesta Key
This Siesta Key waterfront rental is located less than a mile from Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offering easy access to prime Siesta Key attractions.
This 1,000-square-foot apartment features three bedrooms, two bathrooms, and sleeps eight guests, boasting a fully equipped kitchen, free Wi-Fi, a private terrace, and access to a swimming pool, fitness center, and tennis court.

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

Siesta Key Beach - Tropea 665 #3 - Siesta Key, FL
9.4 268 reviews

Siesta Key Beach - Tropea 665 #3

house, Siesta Key
This Siesta Key vacation home is just a short walk from Crescent Beach and a 10-minute drive from the John and Mable Ringling Museum of Art. This highly rated property boasts excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom vacation rental offers a private space for relaxation and a comfortable night's sleep. Guests can enjoy amenities like a fully equipped kitchen, air conditioning, and a spa, along with access to the beach, restaurants, and transportation.
Gulf Villa | 3 Min To #1 Beach | Pool - Siesta Key, FL
9.2 110 reviews

Gulf Villa | 3 Min To #1 Beach | Pool

apartment, Siesta Key
This Siesta Key apartment is just a three-minute walk from the famous Siesta Key Beach and a five-minute walk from the lively Village, putting you right in the heart of the action. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom apartment spans 1500 square feet and features a fully equipped kitchen, a spacious living room with a smart TV, and a private front porch overlooking the Grand Canal. Enjoy the private pool, outdoor area, fishing dock, beach chairs, beach wagon, and beach towels for a relaxing and fun-filled vacation.
Fanta-sea 55 By Beachside Management - Siesta Key, FL
8.6 215 reviews

Fanta-sea 55 By Beachside Management

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.
Sunny & Comfy ~ Steps To Siesta Key Beach ~ Pool! - Siesta Key, FL
9.8 11 reviews

Sunny & Comfy ~ Steps To Siesta Key Beach ~ Pool!

apartment, Siesta Key
This Siesta Key vacation rental is located less than 1.2 miles from Siesta Key Beach, Crescent Beach, and the St. Boniface Episcopal Church Labyrinth, with Siesta Key Marina also nearby.
This two-bedroom, three-bathroom house sleeps eight guests and boasts a private pool, patio, fully equipped kitchen, free WiFi, and convenient barbecue grills, perfect for enjoying the Siesta Key lifestyle.

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.

Siesta Key Condo - Siesta Key, FL
8.7 3 reviews

Siesta Key Condo

apartment, Siesta Key
This Siesta Key condo is steps from a private fishing pier with Sarasota skyline views, a 5-minute walk to Siesta Village, and a 12-minute walk to Beach Access 5.
The two-bedroom, two-bathroom unit sleeps four, features a fully equipped kitchen, in-unit laundry, private balconies in each bedroom, and access to a community pool and kayak launch.
Bayside 2/2 T Model Condo In Sarasota, Perfect For Family Getaways! - Siesta Key, FL
9.4 28 reviews

Bayside 2/2 T Model Condo In Sarasota, Perfect For Family Getaways!

apartment, Siesta Key
This bayside Siesta Key condo, near Siesta Key Beach and St. Armands Circle, offers easy access to both Gulf-side amenities and local attractions.
The 1,090-square-foot unit features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, two pools, a hot tub, and a private patio.
Spacious 2br/2ba Condo At Palm Bay Club, Sarasotaideal For Up To 6 Guests! - Siesta Key, FL
9.4 58 reviews

Spacious 2br/2ba Condo At Palm Bay Club, Sarasotaideal For Up To 6 Guests!

apartment, Siesta Key
This third-floor, gulf-side condominium in Siesta Key is a short walk from the white sand beach, tennis courts, pool, and BBQ area.
This 1140 sq ft condo accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, screened-in patio, and an elevator.
Siesta Key Beachside Condo-direct Beach Access - Siesta Key, FL
9.7 54 reviews

Siesta Key Beachside Condo-direct Beach Access

apartment, Siesta Key
This Siesta Key condo is a one-minute walk from Siesta Key Beach, situated midway between Siesta Key Village and the shops at South Bridge, offering easy access to restaurants and shopping via the free island trolley.
The second-floor unit features one bedroom, one bathroom, a king-size bed and queen-size pull-out sofa sleeping four, a fully equipped kitchen, and includes beach gear (chairs, umbrellas, towels, cooler, cart), plus a heated pool and free 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.

This Newly Renovated And Newly Furnished Second Floor 2 Bedroom 2 Bathroom Condominium - Siesta Key, FL
9.2 40 reviews

This Newly Renovated And Newly Furnished Second Floor 2 Bedroom 2 Bathroom Condominium

apartment, Siesta Key
Everglades Villa  Sleeps 8  Walk To Siesta Beach - Siesta Key, FL
9.2 76 reviews

Everglades Villa Sleeps 8 Walk To Siesta Beach

apartment, Siesta Key
Anchorage Resort 6th Flr 2 Bedroom Condo W Balcony - Siesta Key, FL
9.1 63 reviews

Anchorage Resort 6th Flr 2 Bedroom Condo W Balcony

apartment, Siesta Key
· King Bed .    Pool.    Daily Rentals - Siesta Key, FL
9.7 408 reviews

· King Bed . Pool. Daily Rentals

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.

Siesta Key Oasis| Hot Tub| Fire Pit| Bbq| Games - Siesta Key, FL
10 1 review

Siesta Key Oasis| Hot Tub| Fire Pit| Bbq| Games

apartment, South Sarasota

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.

Beautiful Siesta Key Condo - Two Heated Pools, Tennis, Pickleball, Private Beach Access - Siesta Key, FL
10 1 review

Beautiful Siesta Key Condo - Two Heated Pools, Tennis, Pickleball, Private Beach Access

house, Siesta Key
Relaxing Siesta Key Condo - Pickleball, 2 Heated Pools, Beach Access - Siesta Key, FL
8.0 2 reviews

Relaxing Siesta Key Condo - Pickleball, 2 Heated Pools, Beach Access

house, Siesta Key
Serene Bay Front Condo On Siesta Key - 2 Heated Pools, Pickleball And Tennis, Private Beach Access - Siesta Key, FL
No reviews

Serene Bay Front Condo On Siesta Key - 2 Heated Pools, Pickleball And Tennis, Private Beach Access

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
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