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.

Crescent Arms Condominiums - Siesta Key, FL
9.6 132 reviews

Crescent Arms Condominiums

house, Siesta Key
This house is located in Siesta Key, just a 2.4 kilometre walk from Crescent Beach and a 2.4 kilometre drive from Siesta Key Beach. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The two-bedroom house spans 84 square metres and can comfortably accommodate up to five guests. Amenities include a private beach area, an outdoor pool, a terrace with sea views, a fully equipped kitchen, streaming services, bicycle rental, a picnic area, and a 24-hour front desk.
Coral Breeze | Pet Friendly Home, Heated Pool & Spa, Minutes To Village And Siesta Beach! - Siesta Key, FL
10 8 reviews

Coral Breeze | Pet Friendly Home, Heated Pool & Spa, Minutes To Village And Siesta Beach!

apartment, Siesta Key
This Siesta Key beachfront property is situated less than 1.6km from Irma Beach and Siesta Key Beach, also close to Shell Beach and the Siesta Key Farmers' Market.
This three-bedroom, three-bathroom holiday home offers 177 square metres of living space, comfortably sleeping eight guests with a private pool, Jacuzzi, and free Wi-Fi; gas grills are available for outdoor entertaining.
110 M² Condo ∙ 2 Bedrooms ∙ 5 Guests - Siesta Key, FL
No reviews

110 M² Condo ∙ 2 Bedrooms ∙ 5 Guests

apartment, Siesta Key
This Siesta Key condominium is located in a district with easy access to dining, shopping, and activities, situated a short distance from the beach.
This 110 square metre apartment sleeps up to five guests across two bedrooms and a half-bedroom, offering a heated swimming pool, tennis courts, a fitness centre, and direct access to a private beach with provided loungers and chairs.
Experience Serenity In This 2br, 2ba Condo At Bayside, Sarasota. - Siesta Key, FL
9.6 52 reviews

Experience Serenity In This 2br, 2ba Condo At Bayside, Sarasota.

apartment, Siesta Key
This ground-floor Siesta Key apartment, situated in Palm Bay Club, offers easy access to Siesta Key Beach, a short walk up the Boulevard of Palms, and benefits from the proximity of two swimming pools, tennis courts, and a fitness centre.
The 101-square-metre (1087 sq ft) self-catering property features two bedrooms, two bathrooms, sleeps six guests, and includes amenities such as a fully equipped kitchen, free Wi-Fi, beach chairs and towels, and on-site laundry facilities.

Best family friendly Siesta Key, FL holiday rentals

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

Sol Y Mar | Private Duplex - Two Casitas, Walk To Siesta Keys Crescent Beach, Hoa Pool - Siesta Key, FL
9.6 43 reviews

Sol Y Mar | Private Duplex - Two Casitas, Walk To Siesta Keys Crescent Beach, Hoa Pool

apartment, Siesta Key
This Siesta Key beachfront property is located less than 1.6km from Crescent Beach and Siesta Key Beach, and 3.4km from Turtle Beach, offering convenient access to these popular destinations.
The self-catering house boasts a fully equipped kitchen, private hot tub, in-house laundry facilities, and access to an on-site water park, barbecue grills and parking, perfect for a relaxing family holiday.
62 M² House ∙ 1 Bedroom ∙ 4 Guests - Siesta Key, FL
10 2 reviews

62 M² House ∙ 1 Bedroom ∙ 4 Guests

house, Siesta Key
This beachside cottage, Aloha Kai #63, offers direct access to Crescent Beach, the United States' top-rated beach, and is within walking distance of Siesta Key's restaurants and bars, approximately 0.4 kilometres from local dining and entertainment.
This family-friendly resort accommodation, suitable for four guests, features a 62 square metre layout with one bedroom and one bathroom, complemented by air conditioning, a swimming pool, spa, and on-site amenities including shuffleboard and ping pong, with complimentary beach toys provided.
Our House At The Beach Most See<br>at Siesta Key - Siesta Key, FL
9.5 18 reviews

Our House At The Beach Most See<br>at Siesta Key

apartment, Siesta Key
This Siesta Key holiday home is less than 1.6km from Siesta Key Beach and Siesta Key Beach Playground, and within 3.2km of St Boniface Episcopal Church Labyrinth.
The two-bedroom, two-bathroom property sleeps six, boasting a private pool, tennis court, fully equipped kitchen, free Wi-Fi, and sun loungers with beach towels provided.
Your Dreamoasisawaits: Siestakeyescape With Pool! - Siesta Key, FL
10 127 reviews

Your Dreamoasisawaits: Siestakeyescape With Pool!

apartment, Siesta Key
This Siesta Key holiday home is situated 1.6km from Siesta Key's beaches, offering easy access to the island's attractions.
The two-bedroom, two-bathroom property sleeps six, boasting a private pool, fully equipped kitchen, and open-plan living space with a king-size, queen-size bed and queen-size sofa bed.

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.

Siesta Fiesta - Enjoy Our Updated Beach Paradise! - Siesta Key, FL
10 1 review

Siesta Fiesta - Enjoy Our Updated Beach Paradise!

apartment, Siesta Key
This two-bedroom condominium in Siesta Key offers direct access to the local trolley service, providing car-free journeys to downtown Sarasota, Siesta Key's beaches, and shopping areas.
This Siesta Key apartment accommodates up to six guests and features two en-suite bedrooms, a living area with a fireplace, a lanai with pool views, a heated swimming pool, a pickleball/tennis court, and a fishing dock.
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
This Siesta Key condominium offers a prime location, a mere 7-minute walk to Crescent Beach and directly opposite Siesta Key's renowned #1 Beach, with Sarasota Bradenton International Airport and The John and Mable Ringling Museum of Art both 17.7 kilometres away.
This family-friendly apartment, spanning 89 square metres and accommodating up to 11 guests, boasts a fully equipped kitchen, air conditioning, a swimming pool, a terrace, sauna, spa, fitness centre, tennis court, and on-site parking, with a private beach area and bicycle rental also available for guest use.
Island House Beach Resort 3 - Siesta Key, FL
9.5 339 reviews

Island House Beach Resort 3

house, Siesta Key
This two-bedroom villa is situated just steps from Crescent Beach and a short distance from Siesta Key Beach, offering easy access to the beautiful white sands and turquoise waters of this popular destination. The property has consistently received excellent ratings for its location, cleanliness and overall experience.
The villa is equipped with a fully equipped kitchen, air conditioning, free Wi-Fi and a patio. Enjoy the convenience of home cooking, relax in the comfortable and cool interior, and take advantage of the outdoor space for enjoying the Florida sunshine.
Siesta Key Paradise - Steps To Beach & Village - Siesta Key, FL
10 11 reviews

Siesta Key Paradise - Steps To Beach & Village

apartment, Siesta Key
This Siesta Key flat offers a prime location, mere steps from the USA's number one beach, with dining and shopping within easy walking distance.
This accommodation for up to seven guests boasts three bedrooms, two bathrooms with bidets, air conditioning, a swimming pool, and three grills, ensuring a comfortable stay with entertainment in every room.

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.

Sea Club 2 - Relaxing Siesta Beach Key Condo Rental - Mermaids Rest - Siesta Key, FL
9.8 247 reviews

Sea Club 2 - Relaxing Siesta Beach Key Condo Rental - Mermaids Rest

apartment, Siesta Key
This Siesta Key condo, situated in a gated community approximately 0.4km from a private beach access point, offers easy access to Siesta Key's renowned beaches and nearby restaurants.
The 48-square-metre, one-bedroom apartment sleeps two guests and features a fully equipped kitchen, free Wi-Fi, a private balcony, and access to a heated pool, spa, and on-site parking within a gated complex.
Cabbage Palm Cottage - 1125 - Siesta Key, FL
9.7 14 reviews

Cabbage Palm Cottage - 1125

apartment, Siesta Key
This Siesta Key condo, a short 0.64km stroll from Siesta Beach, offers a beautifully renovated nautical-themed apartment with private heated pool.
The two-bedroom, two-bathroom property sleeps six, includes a fully equipped kitchen, private washer/dryer, two parking spaces, beach equipment, and outdoor seating with a propane grill; an adjacent condo ('Coral Reef') is available for larger groups.
Siesta Key Condo W/ Heated Pool < 1 Mi To Beach - Siesta Key, FL
9.5 20 reviews

Siesta Key Condo W/ Heated Pool < 1 Mi To Beach

house, Siesta Key
This Siesta Key condo is situated less than 1.6km from Crescent Beach and 1.9km from Turtle Beach, offering easy access to these popular Siesta Key beaches and is approximately 16-18km from Sarasota attractions such as St. Armands Circle and the Ringling Museum.
This 90 square metre self-catering apartment features two bedrooms, a fully equipped kitchen including a dishwasher, free Wi-Fi, a private entrance, and access to an on-site heated swimming pool and spa, comfortably accommodating families or groups.
Siesta Key Beach - Bari 665 #2 - Siesta Key, FL
8.9 313 reviews

Siesta Key Beach - Bari 665 #2

apartment, Siesta Key
This apartment is located on Siesta Key, just a short walk from the famous Siesta Key Beach and Crescent Beach, and a 10-mile drive from the John and Mable Ringling Museum of Art. The apartment has received very good user ratings, with excellent scores for location and cleanliness.
The apartment features one bedroom and one bathroom, providing comfortable accommodation for a couple or a small family. Amenities include a fully equipped kitchen, air conditioning, cable TV, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

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.

2 Br Condo In Siesta Key W/ Private Beach Access - Siesta Key, FL
9.9 75 reviews

2 Br Condo In Siesta Key W/ Private Beach Access

apartment, Siesta Key

Best Siesta Key, FL holiday rentals with a balcony

Ocean Views In Our House At The Beach, Full Gulf Views From Balcony, Heated Pools! - Siesta Key, FL
8.8 13 reviews

Ocean Views In Our House At The Beach, Full Gulf Views From Balcony, Heated Pools!

apartment, Siesta Key
Walk To Siesta Key - Siesta Key, FL
No reviews

Walk To Siesta Key

apartment, Siesta Key
Siesta Key Dream Vacation - Siesta Key, FL
9.7 195 reviews

Siesta Key Dream Vacation

apartment, Siesta Key
1 Bedroom 1 1/2 Bathroom Condominium Is Located On The Gulf Side Of Our Property. - Siesta Key, FL
9.4 51 reviews

1 Bedroom 1 1/2 Bathroom Condominium Is Located On The Gulf Side Of Our Property.

apartment, 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 Key Village-suite #1: A Block To The Beach! - Siesta Key, FL
9.8 130 reviews

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

apartment, Siesta Key
Sea Breeze - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach! - Siesta Key, FL
10 45 reviews

Sea Breeze - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach!

apartment, Siesta Key
Walk To Beach/village, Heated Saltwater Pool, Strong Wifi - Siesta Key, FL
9.6 38 reviews

Walk To Beach/village, Heated Saltwater Pool, Strong Wifi

apartment, Siesta Key
Flamingo 1br Beach-side Villa In Siesta Key - Pool - Siesta Key, FL
8.0 4 reviews

Flamingo 1br Beach-side Villa In Siesta Key - Pool

apartment, Siesta Key

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.

Gertrude's Siesta | Bayview Unit W/ Balcony, Pools & Private Beach - Siesta Key, FL
9.2 34 reviews

Gertrude's Siesta | Bayview Unit W/ Balcony, Pools & Private Beach

apartment, Siesta Key
The Beach Club At Siesta #204b - Siesta Key, FL
10 1 review

The Beach Club At Siesta #204b

house, Siesta Key
Relax & Unwind  1br Beach Club Siesta Key 110d Rva - Siesta Key, FL
8.9 1217 reviews

Relax & Unwind 1br Beach Club Siesta Key 110d Rva

apartment, Siesta Key
Charming 2br Bayside Condo In Sarasota, Perfect For A Family Getaway. - Siesta Key, FL
9.2 40 reviews

Charming 2br Bayside Condo In Sarasota, Perfect For A Family Getaway.

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.

Siesta Zen  2br Steps To Siesta Key Beach & Village! - Siesta Key, FL
9.6 70 reviews

Siesta Zen 2br Steps To Siesta Key Beach & Village!

apartment, Siesta Key
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