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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

Beautiful Townhouse 1/2 Block From Siesta Key Village & The Beach! - Siesta Key, FL
9.0 4 reviews

Beautiful Townhouse 1/2 Block From Siesta Key Village & The Beach!

apartment, Siesta Key
This Spanish-style villa is located in Siesta Key Village, just 264 feet from Siesta Key's world-renowned white sand beaches and within easy walking distance of the village's shops and restaurants.
This 2050 square foot residence offers 3 bedrooms, 2 bathrooms, and accommodates up to 8 guests, featuring complimentary bicycles, beach chairs, beach towels, a beach wagon, and access to a partner property pool and hot tub, with included Wi-Fi and TVs in each bedroom and the living room.
Lj's Cottages 4 Balcony Beach And Pool - Siesta Key, FL
9.8 14 reviews

Lj's Cottages 4 Balcony Beach And Pool

apartment, Siesta Key
This beachfront condo rental offers stunning ocean views, situated less than a mile from Crescent Beach and Siesta Key Beach, with Turtle Beach just two miles away.
The two-bedroom, two-bathroom unit sleeps six and includes a fully equipped kitchen, private balcony, in-unit laundry, swimming pool, jacuzzi, and barbecue grills.
2br Renovated Siesta Key Condo, Beach And Pool Access - Siesta Key, FL
9.0 1 review

2br Renovated Siesta Key Condo, Beach And Pool Access

apartment, Siesta Key
This renovated 2-bedroom condo is located in Siesta Key, a 6-minute walk from Crescent Beach, 7.3 miles from Marina Jack, and 11 miles from Sarasota Bradenton International Airport.
This 750 square foot residence accommodates up to 9 guests, offering direct beach and pool access, a fully equipped kitchen, high-speed WiFi, and on-site parking.
Luxury Zen Den With Heated Pool Just Off Siesta Key - Siesta Key, FL
9.4 645 reviews

Luxury Zen Den With Heated Pool Just Off Siesta Key

apartment, Siesta Key
The Zen Den is a short drive from Siesta Key, located in Sarasota, just 6 miles from the Sarasota Opera and 9.4 miles from the John and Mable Ringling Museum of Art. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The Zen Den is a comfortable and well-equipped rental with a private pool, a patio with pool views, a fully equipped kitchen, and streaming services. Guests can enjoy diving nearby, relaxing on the sun terrace, and unwinding in the peaceful garden setting.

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 Beach House - Siesta Key, FL
8.4 73 reviews

Siesta Key Beach House

house, Siesta Key
This Siesta Key villa is located on Crescent Beach, a 6-minute walk from the property, and 11 miles from The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This family-friendly vacation home offers 1410 square feet of living space with 3 bedrooms, 2 bathrooms, and a guest capacity of 8, featuring air conditioning, a private beach area, an outdoor swimming pool, and complimentary WiFi.
Crescent Beach 1015 #4 - Siesta Key, FL
9.3 731 reviews

Crescent Beach 1015 #4

house, Siesta Key
This vacation home is located in Sarasota, just steps from Crescent Beach and a short drive from Turtle Beach, with Sarasota Opera and Marina Jack Restaurant & Marina both being approximately 7.7 miles away. The property has received excellent ratings for user experience, location, and cleanliness.
The home offers two bedrooms, a living room, a fully equipped kitchen, and two bathrooms. It features a private pool, a terrace, a garden, and a spa, as well as internet access, air conditioning, and parking.
Ideal Location Siesta Key Beach Across The Street - Siesta Key, FL
9.9 40 reviews

Ideal Location Siesta Key Beach Across The Street

apartment, Siesta Key
This Siesta Key apartment is located just a 10-minute walk from the beach and St. Boniface Episcopal Church Labyrinth, offering easy access to the area's attractions. Guests consistently rate the apartment excellent for location, cleanliness, and overall experience.
The one-bedroom apartment spans 800 square feet and comfortably accommodates up to 4 guests. Enjoy a fully equipped kitchen, a private balcony with ocean views, a swimming pool, a sauna, and other amenities perfect for a relaxing getaway.
Beachwalk Townhouse With View Of Gulf Of Mexico - Siesta Key, FL
9.6 106 reviews

Beachwalk Townhouse With View Of Gulf Of Mexico

apartment, Siesta Key
This Siesta Key townhouse is just steps from the beach and within walking distance of the village, offering easy access to both relaxation and entertainment. This property consistently receives excellent ratings for location, user experience, and cleanliness.
This 3-bedroom, 2-bathroom vacation rental comfortably accommodates up to 6 guests. Enjoy modern amenities, including a private elevator, heated pool, garage, and full beach gear, making your stay both comfortable and convenient.

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

Comfortable Siesta Key Condo W/ Pool Access! - Siesta Key, FL
8.6 5 reviews

Comfortable Siesta Key Condo W/ Pool Access!

house, Siesta Key
This Siesta Key condo offers a prime location, just a 5-minute walk from Crescent Beach, and is situated 11 miles from The John and Mable Ringling Museum of Art and 7.4 miles from the Sarasota Opera.
This 1100 square foot condominium sleeps up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, complimentary WiFi, and an on-site swimming pool and tennis court.
100 Feet To Siesta Key Beach Best Value! - Siesta Key, FL
9.3 172 reviews

100 Feet To Siesta Key Beach Best Value!

apartment, Siesta Key
This Siesta Key vacation rental is just a minute's walk from the famous white sands of Siesta Key Beach, putting you right in the heart of the action, close to the Village and the main beach entrance. This property consistently receives excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom home comfortably sleeps up to eight guests. It comes equipped with everything you need for a relaxing beach getaway, including a full kitchen, a patio, and beach chairs and towels.
Lj's Cottages 1 - Pool Beach Sunset - Siesta Key, FL
9.6 9 reviews

Lj's Cottages 1 - Pool Beach Sunset

apartment, Siesta Key
This Siesta Key condo rental is less than a mile from Crescent Beach and Siesta Key Beach, and about two miles from Turtle Beach, offering easy access to pristine sands and calm waters.
The three-bedroom, two-bathroom unit sleeps eight guests and features a fully equipped kitchen, private balcony, swimming pool, Jacuzzi, and on-site barbecue grills.
1666 Baywinds Lane, Sarasota, Fl 34231 - Siesta Key, FL
9.7 47 reviews

1666 Baywinds Lane, Sarasota, Fl 34231

apartment, Siesta Key
This Siesta Key vacation home is located just 3 miles from Siesta Key Beach, offering easy access to the renowned sands.
The 1,870-square-foot property features a split floor plan with three bedrooms (two king, one full-size futon), two bathrooms, a private salt-system pool, and a one-car garage.

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.

Adorable Cozy Silver Sands Cottage On Siesta Key!! - Siesta Key, FL
9.8 194 reviews

Adorable Cozy Silver Sands Cottage On Siesta Key!!

apartment, Siesta Key
This charming Siesta Key cottage is just a short walk from the world-renowned Siesta Key Beach, offering a peaceful escape on the intracoastal bay side. The cottage consistently receives excellent ratings for its cleanliness, location, and overall experience.
This cozy vacation rental comfortably sleeps two guests and features a private pool, tiki hut, and fishing dock. Enjoy access to a fully equipped kitchen, high-definition TVs, Wi-Fi, and easy ground floor access.
Heated Pool-short Walk To Beach, Free Trolley Around Siesta Key! - Siesta Key, FL
9.3 27 reviews

Heated Pool-short Walk To Beach, Free Trolley Around Siesta Key!

apartment, Siesta Key
This Siesta Key rental is conveniently located just a short walk from Crescent Beach and about a mile and a half from Siesta Key Beach, making it easy to explore the area's beautiful beaches. The apartment has consistently received excellent ratings for cleanliness, location, and overall experience.
The 1100 square foot apartment comfortably accommodates four guests in two bedrooms. Enjoy the convenience of a fully equipped kitchen, a private balcony with pool views, and a refreshing dip in the heated pool.
Crescent Royale Condominiums108 - Siesta Key, FL
9.0 1 review

Crescent Royale Condominiums108

house, Siesta Key
Crescent Royale 108, a one-bedroom Siesta Key vacation rental, is a four-minute walk from Siesta Key Beach and eleven miles from the John and Mable Ringling Museum of Art.
This 890-square-foot condo features a private balcony, a swimming pool, free Wi-Fi, on-site parking, and can comfortably accommodate up to seven guests.
Lakefront Siesta Key Condo With Private Beach Access - Siesta Key, FL
9.3 3 reviews

Lakefront Siesta Key Condo With Private Beach Access

house, Siesta Key
This Siesta Key condo, an 8-minute walk from Crescent Beach, offers convenient access to Sarasota attractions like the Sarasota International Convention Center (12 miles away) and Marina Jack (7 miles away).
The 1,100-square-foot rental boasts two bedrooms, two bathrooms, and accommodates up to nine guests, featuring a private beach, pool, sauna, fitness center, and tennis court.

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.

Condo On Siesta With Private Pier Near Village - Siesta Key, FL
9.7 16 reviews

Condo On Siesta With Private Pier Near Village

apartment, Siesta Key
Midnight Cove Ii 823 - Siesta Key, FL
8.6 9 reviews

Midnight Cove Ii 823

house, Siesta Key
Recently Updated Cozy Siesta Key Beach Villa - Siesta Key, FL
9.2 29 reviews

Recently Updated Cozy Siesta Key Beach Villa

house, Siesta Key
Jellyfish Unit, Walk To Beach & Siesta Key Village, Pet-friendly - Siesta Key, FL
8.5 2 reviews

Jellyfish Unit, Walk To Beach & Siesta Key Village, Pet-friendly

house, 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.

On Siesta Key Beach! Pool,remodeled! 2bd2ba, Sleeps 6, 3mins From Door To Sand - Siesta Key, FL
10 160 reviews

On Siesta Key Beach! Pool,remodeled! 2bd2ba, Sleeps 6, 3mins From Door To Sand

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.

6415 Midnight Pass #409 - Siesta Key, FL
No reviews

6415 Midnight Pass #409

house, Siesta Key
Gorgeous Bay Views From This Ground Floor Siesta Key Condo - Siesta Key, FL
10 1 review

Gorgeous Bay Views From This Ground Floor Siesta Key Condo

house, Siesta Key
Luxury Bayside Condo – Pool, Tennis & Marina - Siesta Key, FL
No reviews

Luxury Bayside Condo – Pool, Tennis & Marina

apartment, Siesta Key
Spacious 2br Condo On Siesta Key With Private Beach Access - Siesta Key, FL
8.2 6 reviews

Spacious 2br Condo On Siesta Key With Private Beach Access

house, Siesta Key
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