Holiday Rentals in Siesta Key, FL

7731 available vacation rental offers

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Siesta Key, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Siesta Key, FL

Find the Best Seaside Holiday Rentals in Siesta Key, FL

Experience relaxing maritime culture at coastal holiday rentals in Siesta Key, FL, situated a short distance from popular beach communities.

Beachfront Condo - 2-bedroom - Luxury - Directly On Crescent Beach - Siesta Key, FL
9.5 126 reviews

Beachfront Condo - 2-bedroom - Luxury - Directly On Crescent Beach

apartment, Siesta Key
This family-friendly apartment is located on Siesta Key, a short 1.6km walk from Siesta Key Beach and Crescent Beach, with Point of Rocks and Siesta Key Marina within 1.6km. The two-bedroom apartment, which can accommodate up to six guests, offers a fully equipped kitchen, a swimming pool, a spa, a fitness centre, and parking.
Hibiscus Villa  3 Mins To Beach  Pool  Bbq - Siesta Key, FL
9.4 79 reviews

Hibiscus Villa 3 Mins To Beach Pool Bbq

apartment, Siesta Key
This Siesta Key Village villa is located less than 0.8km from Siesta Key Beach (via access points #7 and #5) and a 0.5km stroll from the village centre.
The 84 square metre one-bedroom property sleeps six, boasting a fully equipped kitchen, three 55" Smart TVs, a private patio, and access to a shared heated pool; beach wagon and towels are provided.
Heated Pool, Dock, Kayaks, 1-mile To Turtle Beach - Siesta Key, FL
9.5 35 reviews

Heated Pool, Dock, Kayaks, 1-mile To Turtle Beach

bungalow, Siesta Key
The Hibiscus Bungalow, a one-bedroom self-catering property in Vamo, Siesta Key, Florida, boasts private Heron Lagoon access with kayaks and is conveniently located near Siesta Key's beaches.
This single-storey dwelling offers a queen-size bed, a rollaway bed, a fully equipped kitchen, air conditioning, a private veranda, and access to a shared heated pool and BBQ facilities, comfortably sleeping three guests.
Unit 162- 1 Bedroom 1 1/2 Bathroom Club Side Interior Condominium - Siesta Key, FL
9.4 55 reviews

Unit 162- 1 Bedroom 1 1/2 Bathroom Club Side Interior Condominium

apartment, Siesta Key
This Siesta Key beachfront apartment, a short walk from Siesta Key Beach and Crescent Beach, offers easy access to resort amenities including two swimming pools, tennis courts, and barbeque facilities.
The 90 square metre self-catering property features one bedroom with two queen beds, a living room with a sofa bed accommodating up to four guests, two bathrooms, a fully equipped kitchen, and a screened patio.

Best family friendly Siesta Key, FL holiday rentals

Among the 7731 accommodations in Siesta Key, FL, here are the 4 best family friendly rentals

Siesta Key Village-suite #4: A Block To The Beach! - Siesta Key, FL
9.4 144 reviews

Siesta Key Village-suite #4: A Block To The Beach!

apartment, Siesta Key
This apartment is located in Siesta Key Village, just a block from the famous Siesta Key Beach and a short drive from Crescent Beach, and is 16 kilometres from The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport. It has consistently received excellent ratings for location, cleanliness, and overall experience.
This one-bedroom flat accommodates up to three guests and comes with a fully equipped kitchen, air conditioning, free Wi-Fi, and private parking. Guests can enjoy the convenience of an on-site restaurant and access to a tennis court, making it ideal for families and groups looking for a comfortable and enjoyable stay.
Monarch Villa | Semi Private Pool, Gulf Views, Private Cabana Room, Steps To Siesta Key Beach - Siesta Key, FL
9.8 89 reviews

Monarch Villa | Semi Private Pool, Gulf Views, Private Cabana Room, Steps To Siesta Key Beach

apartment, Siesta Key
This Siesta Key home is located just a mile from the famous Siesta Key Beach, known for its soft, white sand and calm waters, and within easy reach of other beaches like Irma and Crescent. It has received excellent user ratings, making it a popular choice for travellers.
This six-bedroom property comfortably accommodates large families or groups, and includes a sofa bed for extra guests. It features a private swimming pool, a tennis court, a garden, and a game room, alongside modern amenities such as a fully equipped kitchen and free Wi-Fi.
Gertrude's Siesta | Bayview Unit, Near Beach, Private Patio, Heated Pool, Pickle,tennis! - Siesta Key, FL
10 3 reviews

Gertrude's Siesta | Bayview Unit, Near Beach, Private Patio, Heated Pool, Pickle,tennis!

apartment, Siesta Key
This non-smoking flat in Siesta Key is located an 8-minute walk from Siesta Key Public Beach and a 2-minute drive from Crescent Beach, offering convenient access to local attractions and water sports.
This 64 square metre apartment accommodates up to six guests with three bedrooms, a fully equipped kitchen, air conditioning, a shared swimming pool, a private terrace with a barbecue, and a studio space suitable for remote work.
Walk To Siesta Key - Siesta Key, FL
No reviews

Walk To Siesta Key

apartment, Siesta Key
This five-bedroom Siesta Key holiday home is situated a short walk from Siesta Key Beach and within easy reach of St. Armands Circle.
Sleeping up to 15 guests, the property boasts a private pool, full kitchen, laundry facilities, and free parking, alongside a terrace and garden.

Frequently asked questions about holiday 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 plenty of other interesting places to visit. The Siesta Key Drum Circle is a popular spot for live music and entertainment, and you can also visit the Siesta Key Village for shopping and dining. If you're looking for something a bit further afield, you can take a trip to the nearby city of Sarasota, which has a number of museums and art galleries.
  • What are the best Airbnb and holiday rentals in Siesta Key, FL?

  • Which walking or cycling routes are the best in Siesta Key, FL?

    For walking and cycling, the Siesta Key Beach is a great choice. The paved path stretches for 3.5km along the beach, offering stunning views of the Gulf of Mexico. You can also explore the residential areas of Siesta Key, which are full of charming shops and restaurants. For a more challenging ride, consider the Legacy Trail, which runs for 12.5km from Sarasota to Venice.
  • What are the most popular Airbnbs in Siesta Key, FL?

  • What sports or outdoor activites can visitors enjoy in and around Siesta Key, FL?

    Siesta Key is a paradise for outdoor enthusiasts. You can swim, sunbathe, and surf on the beautiful beaches, or try your hand at kayaking or paddleboarding in the calm waters of the Gulf of Mexico. There are also plenty of opportunities for fishing, both from the shore and from a boat. If you're looking for something a bit more adventurous, you can go parasailing or jet skiing.
  • What are the best holiday rentals with a pool in Siesta Key, FL?

  • What other towns or cities can be easily accessed from Siesta Key, FL?

    Siesta Key is conveniently located near several other towns and cities. Sarasota, a vibrant city with a thriving arts scene, is just a short drive away. You can also easily reach Venice, known for its beautiful beaches and historic downtown, and Bradenton, home to the famous Robinson Preserve.
  • What are the best rentals for families and kids in Siesta Key, FL?

  • What amenities are commonly available in vacation rentals in Siesta Key, FL?

    Vacation rentals in Siesta Key typically offer a range of amenities, including private pools, hot tubs, and outdoor grills. Many also have fully equipped kitchens, laundry facilities, and high-speed internet access. Some rentals even offer beach access, making it easy to enjoy the beautiful beaches of Siesta Key.
  • What are the best rentals or Airbnbs with a jacuzzi in Siesta Key, FL?

  • What time of year is best to rent a vacation rental Siesta Key, FL?

    The best time to visit Siesta Key is during the spring or autumn months, when the weather is pleasant and the crowds are smaller. However, if you're looking for a beach vacation, you can enjoy Siesta Key year-round. Just be aware that the summer months can be very hot and humid, and the winter months can be cool and rainy.
  • What are the local dishes in Siesta Key, FL region?

    Siesta Key is known for its fresh seafood, and you'll find plenty of restaurants serving up delicious dishes like grouper sandwiches, shrimp scampi, and stone crabs. You can also enjoy classic American cuisine, such as burgers, fries, and pizza. For a taste of local flavour, try the Key lime pie, a refreshing dessert made with Key lime juice.

Popular destinations

Find the Best Holiday Rentals with a Pool in Siesta Key, FL

Pool access at your holiday rental in Siesta Key, FL provides the perfect complement to a day by the water. Find your ideal stay here.

Unit 148 - 2 Bedroom 2 Bathroom Gulf Side Interior Club Condominium - Siesta Key, FL
9.6 54 reviews

Unit 148 - 2 Bedroom 2 Bathroom Gulf Side Interior Club Condominium

apartment, Siesta Key
This Siesta Key beachfront apartment, situated within the Palm Bay Club, offers direct Gulf-front access to Siesta Key's renowned white sand beach and is a short walk from tennis courts and a fitness centre.
The 106-square-metre (1141 square feet) condo features two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, screened patio, and access to an on-site swimming pool, jacuzzi, and laundry facilities; a beach cart and cooler are provided.
Siesta Home With Pool & Waterslide - Sunset Splash - Siesta Key, FL
9.7 96 reviews

Siesta Home With Pool & Waterslide - Sunset Splash

apartment, Siesta Key
This Siesta Key holiday home is situated in Siesta Key Village, just 3 km from Siesta Key Beach, Irma Beach, and St. Boniface Episcopal Church Labyrinth. It boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The property has 8 bedrooms and 7.5 bathrooms, spanning 331 square metres, providing ample space for large groups or families. Guests can enjoy a private pool, a water park, a spa tub, barbecue grills, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
Cozy 1 Bedroom Condo Steps From Siesta Key Beach! - Siesta Key, FL
9.3 3 reviews

Cozy 1 Bedroom Condo Steps From Siesta Key Beach!

apartment, Siesta Key
This ground-floor Siesta Key apartment is located half a block (approx. 0.08 km) from Siesta Key Beach and minutes from Siesta Key Village, offering easy access to shops, restaurants, and Sarasota International Airport (20 minutes' drive, approx. 16 km).
The self-catering flat features a queen sleeper sofa and king-size bed sleeping up to four guests, a kitchenette, complimentary beach equipment (including bicycles, chairs, and towels), and access to a nearby pool, hot tub, and pickleball courts.
110 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
No reviews

110 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

apartment, Siesta Key
This two-bedroom flat is situated directly opposite the main entrance to Siesta Key Beach, offering immediate access just metres away.
This fully furnished apartment, covering 110 square metres, features two bedrooms, two bathrooms, a full kitchen, air conditioning, a swimming pool, and a balcony, with a minimum two-week rental period and elevator access on the third floor.

Our Favourite Holiday Rentals with Parking in Siesta Key, FL

A car park at your holiday rental in Siesta Key, FL makes reaching the coast and local beaches easy every day with no extra faff.

Luxury Condo Ground Floor Across The Street From The #1 Beach - Siesta Key, FL
9.2 93 reviews

Luxury Condo Ground Floor Across The Street From The #1 Beach

apartment, Siesta Key
This ground floor apartment is located just across the street from Siesta Key's award-winning beach, within easy walking distance of restaurants, bars, and shops. It consistently receives excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
This two-bedroom, two-bathroom apartment offers 93 square metres of space, comfortably accommodating up to six guests. Enjoy a range of amenities including a private lanai, access to a heated swimming pool, and complimentary beach essentials, ensuring a relaxing and enjoyable Siesta Key experience.
Surf Shack- Walk To Village/boat Dock Included - Siesta Key, FL
9.9 98 reviews

Surf Shack- Walk To Village/boat Dock Included

apartment, Siesta Key
This charming cottage is located in a peaceful residential neighbourhood, just a short walk from the stunning Siesta Key Beach and the lively Siesta Key Village, both within 1 kilometre. It boasts excellent user, location, and cleanliness ratings, making it a perfect choice for your Siesta Key getaway.
The cottage comfortably sleeps three guests and features a fully equipped kitchen, a modern bathroom, and a private dock. Enjoy relaxing on the outdoor patio, cooking on the gas grill, or exploring the island on the complimentary bikes.
Siesta Key Beach - Tropea 665 #3 - Siesta Key, FL
9.4 270 reviews

Siesta Key Beach - Tropea 665 #3

house, Siesta Key
This Siesta Key holiday home is just a short walk from Crescent Beach and a 10-minute drive from The John and Mable Ringling Museum of Art, offering a peaceful escape from the bustling tourist areas. Guests consistently rate the property excellent for its location, cleanliness, and overall experience.
The single-bedroom property features a separate bedroom for privacy and a fully equipped kitchen with a dishwasher and oven. Guests can enjoy air conditioning, a TV with cable channels, and access to a spa, restaurant, and parking.
Everglades Villa - Sleeps 8 - Walk To Siesta Beach - Siesta Key, FL
8.0 2 reviews

Everglades Villa - Sleeps 8 - Walk To Siesta Beach

apartment, Siesta Key
This Siesta Key flat offers a prime location, just a 550-metre stroll from Siesta Key Beach, with Marina Jack and Sarasota Opera located 10 kilometres away.
This 107 square metre apartment accommodates up to 15 guests and features a private swimming pool, a fully equipped kitchen with a dishwasher and coffee machine, air conditioning, free WiFi, a terrace, a washer, and a fireplace.

Discover 5-Star Self-Catering Rentals in Siesta Key, FL

Staying in a luxury holiday rental or Airbnb in Siesta Key, FL ensures every detail of your trip feels considered, with high-end finishes and prime locations.

Private Standalone Home - Walk To Siesta Key Beach - Siesta Key, FL
10 107 reviews

Private Standalone Home - Walk To Siesta Key Beach

apartment, Siesta Key

Best Siesta Key, FL holiday rentals with a balcony

Plunge Into Fun & Sun At Siesta Key- A Coastal Gem - Aloha Kai Suite - Roelens - Siesta Key, FL
No reviews

Plunge Into Fun & Sun At Siesta Key- A Coastal Gem - Aloha Kai Suite - Roelens

house, Siesta Key
Siesta Cooler: Only Minutes Walk To Siesta Beach! - Siesta Key, FL
9.5 158 reviews

Siesta Cooler: Only Minutes Walk To Siesta Beach!

apartment, Siesta Key
121 M² House ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
10 123 reviews

121 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Siesta Key
Point Of Rocks - Siesta Key, FL
9.9 32 reviews

Point Of Rocks

house, Siesta Key

Best Pet-Friendly Holiday Rentals in Siesta Key, FL

These dog-friendly holiday rentals and Airbnbs in Siesta Key, FL guarantee a holiday your pet will enjoy as much as you.

Siesta  Beach View : Pineapple Bungalow Efficiency - Siesta Key, FL
10 134 reviews

Siesta Beach View : Pineapple Bungalow Efficiency

apartment, Siesta Key
Villa Paradiso - Private Saltwater Pool - 5 Min To Siesta Key - Siesta Key, FL
10 88 reviews

Villa Paradiso - Private Saltwater Pool - 5 Min To Siesta Key

apartment, South Sarasota
Everglades Villa  Sleeps 8  Walk To Siesta Beach - Siesta Key, FL
9.0 15 reviews

Everglades Villa Sleeps 8 Walk To Siesta Beach

apartment, Siesta Key
Lido Beach Resort - Sarasota - Siesta Key, FL
8.9 1910 reviews

Lido Beach Resort - Sarasota

resort, Sarasota

Search Holiday Rentals with a Hot Tub in Siesta Key, FL

Coming home to a hot tub after a day by the water changes the whole feel of a stay. These holiday rentals are ready for you.

The Beach Club At Siesta #200c - Siesta Key, FL
No reviews

The Beach Club At Siesta #200c

house, Siesta Key
6415 Midnight Pass #210 - Siesta Key, FL
No reviews

6415 Midnight Pass #210

house, Siesta Key
Stunning Lagoon Views And Heated Pool Access - Exquisite Coastal Retreat - Siesta Key, FL
No reviews

Stunning Lagoon Views And Heated Pool Access - Exquisite Coastal Retreat

apartment, Siesta Key
Lj's Cottages 3 - Siesta Key, FL
9.6 257 reviews

Lj's Cottages 3

apartment, Siesta Key

Top-Rated Holiday Rentals with a Spa in Siesta Key, FL

After enjoying everything Siesta Key, FL has to offer, a spa session at your holiday rental is the ideal way to finish the day.

Blue Seas & Sand 2br Beach Club Siesta 200c By Rva - Siesta Key, FL
9.2 62 reviews

Blue Seas & Sand 2br Beach Club Siesta 200c By Rva

apartment, Siesta Key
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