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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

Tiny House Sand Dollar Near Siesta Key - Siesta Key, FL
9.2 81 reviews

Tiny House Sand Dollar Near Siesta Key

house, Gulf Gate Estates
This Gulf Gate Estates home is conveniently located near Gulf Gate Mall, Crescent Beach, and Siesta Key Beach, offering easy access to shopping, dining, and the beautiful Gulf Coast beaches. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom, one-bathroom vacation rental comfortably accommodates up to four guests. The home features a fully equipped kitchen, a patio for relaxing, air conditioning, internet access, and parking, making it ideal for a relaxing getaway.
Waterfront Views, Walk To Everything Pool, Pool - Siesta Key, FL
9.2 28 reviews

Waterfront Views, Walk To Everything Pool, Pool

apartment, Siesta Key
This beachfront condo rental on Siesta Key offers stunning ocean views, a short walk from Siesta Key Beach and Crescent Beach, and within one mile of Siesta Key Marina and Point of Rocks.
This 860-square-foot, two-bedroom, two-bathroom unit sleeps four and includes a fully equipped kitchen, private terrace, access to a swimming pool, fitness center, and tennis court, plus on-site BBQ 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.
Lj's Cottages 3 - Balcony Beach Pool Sand Sunsets - Siesta Key, FL
9.2 15 reviews

Lj's Cottages 3 - Balcony Beach Pool Sand Sunsets

apartment, Siesta Key
This Siesta Key beachfront condo is conveniently located near Crescent Beach (within 1 mile) and Turtle Beach (2 miles), offering easy access to Siesta Key's pristine sands.
This 3-bedroom, 2-bathroom vacation rental sleeps 8 guests and boasts a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and barbecue grills; enjoy the on-site hot tub and proximity to numerous beach activities.

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 Front 2 Bedroom  Condo W/ Parking - Siesta Key, FL
9.9 63 reviews

Siesta Key Beach Front 2 Bedroom Condo W/ Parking

apartment, Siesta Key
This Siesta Key apartment is located just steps away from the famous white sand beaches and a short walk from the downtown area, offering a peaceful and convenient location. The apartment consistently receives excellent ratings for cleanliness, location, and user experience.
The apartment features two bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy modern amenities such as a fully equipped kitchen, air conditioning, a private garden, and reserved parking.
*Eclectic Hidden Gem / Tiki Bar And Pool* - Siesta Key, FL
10 10 reviews

*Eclectic Hidden Gem / Tiki Bar And Pool*

apartment, Gulf Gate Estates
This Gulf Gate Estates rental is a short 19-minute walk from Crescent Beach and 10 miles from The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This recently renovated 1,000-square-foot apartment features two bedrooms, two bathrooms, accommodates six guests, and includes a private terrace, swimming pool, tiki bar, free Wi-Fi, and private parking.
Crescent Cottage | Pool + Walk To Crescent Beach - Siesta Key, FL
9.5 148 reviews

Crescent Cottage | Pool + Walk To Crescent Beach

house, Siesta Key
This smoke-free vacation home is located in Siesta Key, a 5-minute walk from Point of Rocks and Crescent Beach, and within 2 miles of Siesta Key Beach and Turtle Beach. It has excellent user, location, and cleanliness ratings.
The house has 9 bathrooms, a sofa bed, a kitchen with a fridge, freezer, microwave oven, and dishwasher, a dining area, a TV, and barbecue grills. It also has air conditioning, a swimming pool, parking, internet, and a private pool by the sea. Pets are allowed.
Siesta Key Oasis-spectacular With Heated Pool/spa And Steps To Beach And Village - Siesta Key, FL
10 38 reviews

Siesta Key Oasis-spectacular With Heated Pool/spa And Steps To Beach And Village

apartment, Siesta Key
This 3-bedroom, 2-bathroom condo in Siesta Key is a 7-minute walk from Siesta Key Beach and close to Siesta Key Village's shops and restaurants.
This pet-friendly rental accommodates up to 6 guests and features a private heated pool, spa, outdoor dining area with a waterfall, and 75 ft. of canal access, with complimentary bikes and beach gear provided.

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

Private Beach Getaway Near Point Of Rocks - Siesta Key, FL
9.9 23 reviews

Private Beach Getaway Near Point Of Rocks

apartment, Siesta Key
This Siesta Key condo rental is conveniently located near Siesta Key Beach, within one mile of Siesta Key Marina, and less than a 15-minute drive from Crescent Beach and Point of Rocks.
The two-bedroom, two-bathroom unit features a fully equipped kitchen, private balcony, in-unit coffee/tea maker, and TV; guests can also enjoy the on-site swimming pool and pet-friendly policy.
Siesta Key Village-suite #1: A Block To The Beach! - Siesta Key, FL
9.8 132 reviews

Siesta Key Village-suite #1: A Block To The Beach!

apartment, Siesta Key
This Siesta Key apartment is just a 4-minute walk from the famous Siesta Key Beach and 1.3 miles from Crescent Beach, putting you right in the heart of the action. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers a comfortable 900 square feet of living space with one bedroom and one bathroom. You'll have access to a fully equipped kitchen, a private outdoor seating area, and a range of amenities like a swimming pool, tennis court, and laundry service.
Villa 2 Walk To Siesta Beach, Pool, Daily Rentals - Siesta Key, FL
9.6 11 reviews

Villa 2 Walk To Siesta Beach, Pool, Daily Rentals

apartment, Siesta Key
This Siesta Key condo is located in Sarasota, a short walk from Crescent Beach and 11 miles from the John and Mable Ringling Museum of Art.
This 500-square-foot unit features 1 bedroom, 1 bathroom, and accommodates up to 3 guests, offering a kitchenette, outdoor swimming pool, complimentary private parking, and free WiFi.
Siesta Key Beach 665 #1 - Siesta Key, FL
9.2 289 reviews

Siesta Key Beach 665 #1

house, Siesta Key
This Siesta Key vacation rental is just steps from the famous Siesta Key Beach and an 11-minute walk from Crescent Beach, offering easy access to the area's best attractions. Guests consistently rate this property excellent for location, cleanliness, and overall experience.
The two-bedroom house provides 1000 square feet of space for your vacation. Enjoy the convenience of air conditioning, a fully equipped kitchen with a dishwasher, and a spa, all while being steps away from the beach.

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.

2br Villa, Private Beach, Heated Pool - Siesta Key - Siesta Key, FL
10 4 reviews

2br Villa, Private Beach, Heated Pool - Siesta Key

house, Siesta Key
This 2-bedroom, 1-bathroom villa is located centrally on Siesta Key, a short walk from Crescent Beach and 0.5 miles from Siesta Key's dining and shopping.
This vacation rental accommodates up to 6 guests and features a resort-style swimming pool, a garden, and parking.
Siesta Sanctuary - Siesta Key, FL
9.9 41 reviews

Siesta Sanctuary

apartment, Siesta Key
Sea Winds #104, a ground-floor condo in Sarasota's Siesta Key, offers easy access to award-winning beaches and the Gulf of Mexico via a short walk or trolley ride.
This two-bedroom, one-bathroom unit sleeps six, features a patio, swimming pool, parking, and is turnkey with updated amenities including air conditioning and internet access; nearby shops, bars, and restaurants provide ample entertainment options.
· King Bed .    Pool.    Daily Rentals - Siesta Key, FL
9.7 419 reviews

· King Bed . Pool. Daily Rentals

apartment, Siesta Key
This Siesta Key apartment is located just a short walk from the Siesta Key Marina and Crescent Beach, making it a great base for exploring the area. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom unit can comfortably accommodate up to two guests and features a kitchenette with a fridge and microwave, allowing for easy meal preparation. Amenities include air conditioning, a swimming pool, a garden, and parking, ensuring a comfortable and enjoyable stay.
The Beach Club At Siesta #100b - Siesta Key, FL
10 1 review

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.

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.

Our Third Floor Condo Is A Quiet Escape Nestled Amid Lush Tropical Landscaping - Siesta Key, FL
9.6 81 reviews

Our Third Floor Condo Is A Quiet Escape Nestled Amid Lush Tropical Landscaping

apartment, Siesta Key
Charming 2br Condo On Siesta Key - Gbb 1240 - Siesta Key, FL
10 11 reviews

Charming 2br Condo On Siesta Key - Gbb 1240

apartment, Siesta Key
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
Vacation Home Away From Home At Bay Oaks D41 - Siesta Key, FL
8.7 6 reviews

Vacation Home Away From Home At Bay Oaks D41

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.

Just Renovated 2bed/2bath Siesta Key Beach Condo - Siesta Key, FL
10 44 reviews

Just Renovated 2bed/2bath Siesta Key Beach Condo

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.

Upscale Complex Near Beach And Bay With Tennis, Fitness Room, Pool, Hot Tub - Siesta Key, FL
No reviews

Upscale Complex Near Beach And Bay With Tennis, Fitness Room, Pool, Hot Tub

apartment, Siesta Key
Lakefront Siesta Key Condo With Beach Access - Siesta Key, FL
9.0 3 reviews

Lakefront Siesta Key Condo With Beach Access

house, Siesta Key
Newly Renovated* Townhome In Prime Location - Siesta Key, FL
9.8 90 reviews

Newly Renovated* Townhome In Prime Location

apartment, Siesta Key
Stunning Beachfront Condo With Panoramic Views, Pickelball, And Dual Masters - Siesta Key, FL
No reviews

Stunning Beachfront Condo With Panoramic Views, Pickelball, And Dual Masters

apartment, Siesta Key