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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

Newly Remodeled 8-steps To Sand Path Of Beach! - Siesta Key, FL
9.5 11 reviews

Newly Remodeled 8-steps To Sand Path Of Beach!

apartment, Siesta Key
This Siesta Key apartment rental is conveniently located a short walk from Crescent Beach and 1.2 miles from Turtle Beach, with the Ringling Museum and Sarasota Opera House within easy driving distance.
The 600-square-foot unit features one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, Wi-Fi, private parking, and a terrace; on-site amenities include a shared lounge, picnic area, and laundry facilities.
Sundeck With Ocean View, Private Access To Beach & 500ft To The Village - Siesta Key, FL
10 14 reviews

Sundeck With Ocean View, Private Access To Beach & 500ft To The Village

apartment, Siesta Key
This Siesta Key beachfront condo is located in Siesta Key Village, less than a mile from the Siesta Key Farmers Market and Siesta Key Beach, and within two miles of Irma Beach and the Siesta Key Beach Playground.
This 1,600-square-foot rental boasts four bedrooms, two bathrooms, and accommodates up to ten guests, featuring a private balcony, fireplace, fully equipped kitchen, and free Wi-Fi.
Topsail Cottage | Sk Home W/ Rooftop Views Of Gulf - Siesta Key, FL
9.8 52 reviews

Topsail Cottage | Sk Home W/ Rooftop Views Of Gulf

house, Siesta Key
This beachfront vacation home is located near Siesta Key Beach, less than a mile from Point of Rocks, and a 15-minute drive from Crescent Beach and Siesta Key Marina.
This 3,350-square-foot house features four bedrooms, four bathrooms, and sleeps up to 12 guests, offering a rooftop terrace, a private pool, and gas grills.
Siesta Key Island Rentals - Siesta Key, FL
9.8 751 reviews

Siesta Key Island Rentals

house, Siesta Key
This beautiful home is located on Siesta Key, just a short distance from both Siesta Key Beach and Crescent Beach, offering easy access to the area's famous white sand and clear waters. It boasts excellent user, location, and cleanliness ratings, making it a top choice for travelers.
The property features a private swimming pool, a Jacuzzi, a terrace, and a garden, perfect for relaxing and enjoying the Florida sunshine. Guests can also enjoy a variety of activities, including swimming, diving, fishing, and tennis.

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
8.5 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.
Vinca | Steps To Siesta Key Village! - Siesta Key, FL
9.5 111 reviews

Vinca | Steps To Siesta Key Village!

house, Siesta Key
This vacation home is located in Siesta Key Village, just a short walk from the famous Siesta Key Beach and other popular beaches, as well as local attractions and restaurants. The property has received excellent ratings for location, cleanliness, and overall experience.
This rental offers a fully equipped kitchen, a comfortable living area with a sofa bed, and a dining area. The home also features a swimming pool, terrace, garden, and parking, perfect for enjoying the beautiful Siesta Key weather.
House ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
10 3 reviews

House ∙ 2 Bedrooms ∙ 6 Guests

house, Siesta Key
Aloha Kai #49 is a 2-bedroom, 1-bathroom condo located within the gated Aloha Kai resort on Crescent Beach, offering direct access to the #1 rated beach in the U.S. and a short walk to Siesta Key's dining and entertainment.
This family-friendly unit accommodates up to 6 guests and features air conditioning, internet, a full kitchen, access to the largest pool on Siesta Key, and complimentary beach toys, with community amenities like shuffleboard and ping pong available.
Stunning Sunset Views-steps To Siesta Key Beach-a Couples' Romantic Beach Condo - Siesta Key, FL
9.8 138 reviews

Stunning Sunset Views-steps To Siesta Key Beach-a Couples' Romantic Beach Condo

apartment, Siesta Key
This Siesta Key apartment is located just a short walk from the famous Siesta Key Beach and within a mile of St. Boniface Episcopal Church Labyrinth. The apartment has excellent user ratings and is perfect for families or groups of friends.
The apartment has one bedroom and one bathroom and is 790 square feet. It offers a fully equipped kitchen, a swimming pool, a spa, a tennis court, and a terrace or balcony.

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 2-bedroom Condo With Pool - Siesta Key, FL
9.4 57 reviews

Siesta Key 2-bedroom Condo With Pool

house, Siesta Key
This recently renovated Sarasota condo is conveniently located near Crescent Beach, a short 1.2-mile drive from Turtle Beach and 11 miles from The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 900-square-foot vacation home features two bedrooms, two bathrooms, a private pool, and a fully equipped kitchen, comfortably accommodating families or small groups; free Wi-Fi and parking are included.
Cozy 1-bedroom Condo A Short Walk To Siesta Key Beach - Siesta Key, FL
9.8 39 reviews

Cozy 1-bedroom Condo A Short Walk To Siesta Key Beach

apartment, Siesta Key
This Siesta Key waterfront condo offers stunning views and is a short 15-minute walk from Siesta Key Beach and Crescent Beach, and less than a mile from Siesta Key Marina.
The one-bedroom, one-bathroom apartment sleeps four guests and features a fully equipped kitchen, in-unit laundry, a balcony, and a swimming pool; enjoy nearby beach access and water activities.
Updated Siesta Key Vacation Rental At Bay Oaks - Siesta Key, FL
9.4 21 reviews

Updated Siesta Key Vacation Rental At Bay Oaks

apartment, Siesta Key
This two-bedroom, two-bathroom condo in the Bay Oaks community on Siesta Key is a short walk from Siesta Key Public Beach and half a mile from South Village's shops and restaurants.
The fully renovated unit sleeps five, features a fully equipped kitchen, in-unit laundry, and access to Bay Oaks' heated pool, tennis courts, and barbecue area, plus one carport parking space and additional guest parking.
70 M² Condo ∙ 1 Bedroom ∙ 2 Guests - Siesta Key, FL
No reviews

70 M² Condo ∙ 1 Bedroom ∙ 2 Guests

apartment, Siesta Key
This one-bedroom condo in the Aloha Kai resort is located directly on Crescent Beach, a district of Siesta Key renowned as the #1 beach in the U.S., and is within walking distance to numerous restaurants, ice cream parlors, and bars accessible by foot or the Siesta Key trolley.
This 740 square foot unit accommodates up to two guests and features air conditioning, a full kitchen, a private patio with Gulf of Mexico views, direct beach access with provided shaded pavilions and lounge chairs, and access to the largest pool on Siesta Key along with on-site shuffleboard and ping pong.

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.

Skv 311 - Pool  Short Walk To Beach & Village - Siesta Key, FL
9.5 108 reviews

Skv 311 - Pool Short Walk To Beach & Village

apartment, Siesta Key
This Siesta Key apartment is located just a short walk from the famous Siesta Key Beach, offering a peaceful escape from the bustling village while still being close to all the action. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom apartment spans 1000 square feet, comfortably accommodating up to six guests. Enjoy a private pool, a balcony, a terrace, a barbecue, and a fully equipped kitchen, perfect for relaxing and enjoying your Siesta Key vacation.
3bed Home Siesta Key Beach - Siesta Key, FL
10 40 reviews

3bed Home Siesta Key Beach

house, Siesta Key
This Gulf Gate Estates townhouse, a 15-minute walk from Siesta Key Beach, offers a convenient location near local amenities.
The three-bedroom, two-bathroom home sleeps eight guests and features a fully equipped kitchen, swimming pool, and private parking.
2bedroom/2bath Steps Away From Siesta Key Beach! - Siesta Key, FL
10 4 reviews

2bedroom/2bath Steps Away From Siesta Key Beach!

house, Siesta Key
This 2-bedroom, 2-bathroom vacation home in Siesta Key's Point of Rocks area is steps from a shared heated pool and a short walk to Siesta Key Beach and Crescent Village.
This rental accommodates up to 6 guests and includes internet, air conditioning, a kitchen with a fridge and microwave, a garden, and complimentary bicycles, beach chairs, towels, a beach wagon, and a cooler, with access to on-site charcoal BBQ grills and Siesta Beach Pickleball Courts.
Siesta Key Vacation Rental Home Close To Village With Swimming Pool And Free Wifi - Siesta Key, FL
9.4 18 reviews

Siesta Key Vacation Rental Home Close To Village With Swimming Pool And Free Wifi

apartment, Siesta Key
This Siesta Key vacation home boasts a central location on the barrier island, offering easy access to Siesta Key Beach, Turtle Beach, St. Armands Circle, and the Mall at University Town Center.
This 1910-square-foot rental features a spacious open floor plan, sleeps up to 10 guests in 3 bedrooms and 2 bathrooms, and includes a private saltwater pool, fully equipped kitchen, and extensive beach gear.

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.

Walk To The Beach Or Village In Minutes! - Siesta Key, FL
9.5 90 reviews

Walk To The Beach Or Village In Minutes!

house, Siesta Key
Waterfront Living | 30' Boat/jet Ski Dock Slip | Beach Access | Pool | Tennis | In-unit Laundry - Siesta Key, FL
9.8 16 reviews

Waterfront Living | 30' Boat/jet Ski Dock Slip | Beach Access | Pool | Tennis | In-unit Laundry

apartment, Siesta Key
Rustic Beach Hideaway - Siesta Key, FL
10 3 reviews

Rustic Beach Hideaway

apartment, Siesta Key
6415 Midnight Pass #311 - Siesta Key, FL
No reviews

6415 Midnight Pass #311

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.

2 Br Condo In Siesta Key W/ Private Beach Access - Siesta Key, FL
9.9 72 reviews

2 Br Condo In Siesta Key W/ Private Beach Access

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.

Tropical 2-bdr Condo With Pool On Siesta Key Beach - Siesta Key, FL
No reviews

Tropical 2-bdr Condo With Pool On Siesta Key Beach

apartment, Siesta Key
Gbb 1274 Spacious 2br 2nd Floor Siesta Key Condo - Siesta Key, FL
9.5 2 reviews

Gbb 1274 Spacious 2br 2nd Floor Siesta Key Condo

house, Siesta Key
Walk To Siesta Key Beach - Family & Pet Friendly - Private Saltwater Pool - Fenced Yard -Gourmet Wolf Subzero Kitchen -Garage -Close To Restaurants Shops-aylees Private Beach House - Siesta Key, FL
No reviews

Walk To Siesta Key Beach - Family & Pet Friendly - Private Saltwater Pool - Fenced Yard -Gourmet Wolf Subzero Kitchen -Garage -Close To Restaurants Shops-aylees Private Beach House

house, Siesta Key
Spacious 1st-floor Siesta Key Condo Across From #1 Beach - Villa Maritima - Siesta Key, FL
10 2 reviews

Spacious 1st-floor Siesta Key Condo Across From #1 Beach - Villa Maritima

apartment, Siesta Key
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