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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

Best Value 1br  Walk To Beach, Dining & Nightlife! - Siesta Key, FL
9.6 32 reviews

Best Value 1br Walk To Beach, Dining & Nightlife!

apartment, Siesta Key
This Siesta Key beachfront rental is less than a mile from Crescent Beach and Siesta Key Beach, and about two miles from Turtle Beach.
The one-bedroom, one-bathroom apartment sleeps four, features a full kitchen with dishwasher, in-unit laundry, a balcony, free parking, and complimentary Wi-Fi.
Next To The Beach - Our House At The Beach W-103 - Siesta Key, FL
9.4 3 reviews

Next To The Beach - Our House At The Beach W-103

apartment, Siesta Key
This beachfront Siesta Key condo offers direct beach access, a 10-minute walk from Siesta Key Beach Playground and Beach, and is less than a mile from St. Boniface Episcopal Church Labyrinth and the Siesta Key Farmers Market.
This 1190-square-foot rental boasts two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, in-unit laundry, private balcony, swimming pool, spa, and tennis court.
Casa Van Lopik Jardin- Tiki-bar, Balcony, Tropical Patio, 250 Steps To Beach And Village! - Siesta Key, FL
9.0 2 reviews

Casa Van Lopik Jardin- Tiki-bar, Balcony, Tropical Patio, 250 Steps To Beach And Village!

house, Siesta Key
Casa Van Lopik Jardin is a Siesta Key vacation rental, a 250-step walk from Siesta Key Beach and the village, offering easy access to nearby attractions like Crescent Beach (1.2 miles) and the John and Mable Ringling Museum of Art (10 miles).
This 1190-square-foot house features three bedrooms, two bathrooms, sleeps 23 guests, includes a private Tiki bar, balcony, tropical patio, fully equipped kitchen, free Wi-Fi, and free parking.
Amazing Siesta Key Condo In Midnight Cove Ii - Siesta Key, FL
9.3 91 reviews

Amazing Siesta Key Condo In Midnight Cove Ii

apartment, Siesta Key
This Siesta Key condo is conveniently located just a short walk from the famous Crescent Beach and a short distance from Siesta Key Village, offering easy access to the island's best attractions. The apartment has received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
This 2-bedroom, 840-square-foot apartment comfortably accommodates up to four guests. Enjoy the convenience of a fully equipped kitchen, a private balcony with waterway views, and access to a range of amenities including a swimming pool, jacuzzi, fitness center, and more.

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.

84 M² Villa ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
10 6 reviews

84 M² Villa ∙ 2 Bedrooms ∙ 6 Guests

house, Siesta Key
This Gulfside unit B07 at Casa Blanca resort is situated a short walk from the #1 rated Siesta Key beach and midway to the complex pool.
This 900 sq ft vacation rental accommodates up to 6 guests with 2 bedrooms, 1 bathroom, a king bed, two twin beds, a queen sofa bed, and features a private lanai, 3 smart TVs, complimentary WiFi, and an outdoor hot/cold shower.
Siesta Harbor Portofino Canal View - Siesta Key, FL
9.8 13 reviews

Siesta Harbor Portofino Canal View

apartment, Siesta Key
This 1100+ sq ft, 2-bedroom, 2-bathroom condo in Siesta Harbor offers tranquil canal water views and is located directly across from Crescent Beach, with private gated access just a 6-minute walk away.
This family-friendly apartment boasts a heated swimming pool, hot tub, fitness center, tennis court, and is equipped with a full kitchen, air conditioning, internet, and covered parking, accommodating up to 6 guests.
Crescent Beach 1011 #1 - Siesta Key, FL
9.3 735 reviews

Crescent Beach 1011 #1

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.
Unit 161- Palm Bay Club, Beautiful Gulf Side Condo - Siesta Key, FL
No reviews

Unit 161- Palm Bay Club, Beautiful Gulf Side Condo

apartment, Siesta Key
This top-floor condominium offers direct, seconds-away access to Siesta Key Beach, renowned as the best in the USA, on the Gulf side of Siesta Key.
This family-friendly, two-bedroom, two-bathroom condo accommodates up to six guests, featuring a fully equipped kitchen, in-unit washer and dryer, a patio, and spa amenities.

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

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.
Lantana - 5251a - Siesta Key, FL
9.3 3 reviews

Lantana - 5251a

house, Siesta Key
Lantana - 5251A is a vacation home located just a 5-minute walk from the beautiful Siesta Key Beach, with Crescent Beach a short drive away. The home has earned excellent user and location ratings, and a good cleanliness rating.
The two-bedroom, two-bathroom home offers 740 square feet of space, comfortably accommodating up to six guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a swimming pool, and free parking, making it easy to relax and explore all that Siesta Key has to offer.
Siesta Key 2br Villa With Shared Pool And Dock - Siesta Key, FL
9.6 15 reviews

Siesta Key 2br Villa With Shared Pool And Dock

apartment, Siesta Key
This Siesta Key vacation home is just a 15-minute walk from Siesta Key Beach and Crescent Beach, putting you close to the area's most popular beaches. Guests consistently rate this property excellent for location, cleanliness, and overall experience. This 1500 square foot house has 2 bedrooms, 2 bathrooms, and comfortably sleeps 5 guests. Enjoy a private kitchen, a swimming pool, a garden, and concierge services, along with free Wi-Fi and convenient limo/town car service.
Quaint 2-bedroom House With Ac In Sunny Sarasota, Minutes From Siesta Key - Siesta Key, FL
No reviews

Quaint 2-bedroom House With Ac In Sunny Sarasota, Minutes From Siesta Key

apartment, Siesta Key
This 2-bedroom, 1-bathroom condo in Sarasota is located just minutes from Siesta Key Beach and offers convenient access to St. Armands Circle and the Mall at University Town Center.
This family-friendly accommodation sleeps up to 4 guests and features air conditioning, a fully equipped kitchen with a fridge, microwave, and dishwasher, and parking.

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.

Jamaica Royale Villa: Modern 1br Retreat  Sleeps 6 With Private Beach Access And Vip Perks Daily! - Siesta Key, FL
9.6 58 reviews

Jamaica Royale Villa: Modern 1br Retreat Sleeps 6 With Private Beach Access And Vip Perks Daily!

apartment, Siesta Key
This beachfront Siesta Key condo, located in the city center, is a 10-minute walk from St. Boniface Episcopal Church Labyrinth and Siesta Key Beach, and within 2 miles of Crescent Beach and Siesta Key Marina.
This 730-square-foot apartment features one bedroom, one bathroom, sleeps six guests, and includes a fully equipped kitchen, in-unit laundry, private patio, free WiFi, and access to a swimming pool and tennis court.
Charm | Comfy | Tiki | Pool Private Beach - Siesta Key, FL
9.6 283 reviews

Charm | Comfy | Tiki | Pool Private Beach

apartment, Siesta Key
This Siesta Key condo is located directly on the beach, just a short walk from Siesta Key Beach and Crescent Beach. The surrounding area offers a mix of relaxation and activity, perfect for enjoying the Florida sunshine. This apartment is highly rated, with excellent reviews for location, cleanliness, and overall experience.
The condo features one bedroom and one bathroom, providing comfortable accommodations for up to four guests. Amenities include a fully equipped kitchen, a private balcony, access to a swimming pool, and a spa. Enjoy the convenience of a washer and dryer, a garden area, and barbecue grills.
Siesta Key Beachfront Retreat With Gulf Views - Siesta Key, FL
No reviews

Siesta Key Beachfront Retreat With Gulf Views

apartment, Siesta Key
This Siesta Key condominium offers direct Gulf-front access and is located steps from Crescent Beach, 11 miles from the Ringling Museum and Sarasota Airport.
This 1830 sq ft residence accommodates up to 11 guests with three bedrooms, three bathrooms, a fully equipped kitchen, a swimming pool, hot tub, sauna, fitness center, bar, garden, and private parking.
Fully Renovated Condo On Bay | Resort Amenities - Siesta Key, FL
9.7 6 reviews

Fully Renovated Condo On Bay | Resort Amenities

apartment, Siesta Key
This renovated two-bedroom, two-bathroom condo at Harbor Towers Yacht & Club in Siesta Key is less than a 0.75-mile walk to both Siesta Key Beach and Crescent Beach.
This unit accommodates up to six guests and offers resort-style amenities, including two heated swimming pools, three Har-Tru Clay tennis courts, a state-of-the-art exercise room, and access to fishing and boat docks, with complimentary daily admission to area attractions provided through Xplorie's program.

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.

Paradise In Siesta! - Siesta Key, FL
9.9 44 reviews

Paradise In Siesta!

house, Siesta Key
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
Renovated Siesta Key Condo, Beach/pool Access - Siesta Key, FL
9.9 92 reviews

Renovated Siesta Key Condo, Beach/pool Access

apartment, Siesta Key
New  Serene Retreat | Private Patio & Pool - Siesta Key, FL
9.8 142 reviews

New Serene Retreat | Private Patio & Pool

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.

Sunshine On Siesta - Siesta Key, FL
10 1 review

Sunshine On Siesta

house, 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.

Garden View Siesta Key Condo - Pickleball, 2 Pools, Beach Access - Siesta Key, FL
9.0 1 review

Garden View Siesta Key Condo - Pickleball, 2 Pools, Beach Access

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
163 M² Condo ∙ 3 Bedrooms ∙ 6 Guests - Siesta Key, FL
10 1 review

163 M² Condo ∙ 3 Bedrooms ∙ 6 Guests

apartment, Siesta Key
3br Oceanfront Luxury Condo At The Hyatt Residences On Siesta Key Beach - Ocean Eyes - Siesta Key, FL
9.8 9 reviews

3br Oceanfront Luxury Condo At The Hyatt Residences On Siesta Key Beach - Ocean Eyes

apartment, Siesta Key
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