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

Best family friendly Siesta Key, FL holiday rentals

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

Beach Rd, 300ft To Beach Access & 500ft To Siesta Key Village, 1bdr - Siesta Key, FL
9.0 3 reviews

Beach Rd, 300ft To Beach Access & 500ft To Siesta Key Village, 1bdr

house, Siesta Key
This beachfront apartment in Siesta Key Village offers direct beach access, a short walk from Siesta Key Beach, 1.8km from Crescent Beach, and 16km from The John and Mable Ringling Museum of Art.
The 56 square metre property features one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, private patio, barbecue facilities, and free private parking; baby safety gates are also provided.
Siesta Key Village  Pool  Walk To Beach  Pets - Siesta Key, FL
9.4 15 reviews

Siesta Key Village Pool Walk To Beach Pets

apartment, Siesta Key
This Siesta Key apartment, a short 1.6km stroll from Siesta Key Beach and the Siesta Key Farmers' Market, offers easy access to Irma and Shell Beaches within a 3.2km radius.
The 71 square metre self-catering property sleeps four guests in two bedrooms and one bathroom, boasting a private patio, swimming pool, and in-unit laundry facilities.
Lakefront Siesta Key Condo With Beach Access - Siesta Key, FL
9.0 3 reviews

Lakefront Siesta Key Condo With Beach Access

house, Siesta Key
This Siesta Key condo, near Crescent Beach (0.6km) and 17km from the John and Mable Ringling Museum of Art, offers direct beach access.
The 139 square metre property boasts three bedrooms, two bathrooms, sleeping six, and features a terrace, sauna, fitness centre, tennis court, parking, and free Wi-Fi.
Sunrise Porch Lookout - Sk Collection Siesta Key - Siesta Key, FL
9.0 1 review

Sunrise Porch Lookout - Sk Collection Siesta Key

apartment, Siesta Key
Sunrise Porch Lookout is a holiday flat located in Siesta Key, a 6-minute walk from Crescent Beach and 17.7 kilometres from the John and Mable Ringling Museum of Art.
This 70 square metre holiday flat accommodates up to three guests and features a fully equipped kitchen, private balcony, air conditioning, complimentary WiFi, free private parking, and access to a year-round outdoor swimming pool with direct access to a private beach area.

Best Siesta Key, FL holiday rentals with a pool

Among the 7731 accommodations in Siesta Key, FL, here are the 4 best rentals with a pool

Vista Hermosa Third Floor - Elevator - Siesta Key, FL
10 11 reviews

Vista Hermosa Third Floor - Elevator

house, Siesta Key
This Siesta Key apartment is less than 1.6km from Crescent Beach and Siesta Key Beach, and approximately 3km from Turtle Beach, offering easy access to three stunning beaches.
This three-bedroom, two-bathroom property boasts 93 square metres of floor space, sleeps six guests, and includes a fully equipped kitchen, swimming pool, tennis court, free Wi-Fi, and on-site barbecue facilities.
Siesta Key Couple's Get Away!!! - Siesta Key, FL
9.8 137 reviews

Siesta Key Couple's Get Away!!!

apartment, Siesta Key
This Siesta Key apartment is situated less than 1.6km from Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offering easy access to pristine sands and watersports.
The self-catering flat, sleeping two guests in one bedroom and one bathroom, includes a fully equipped kitchen, air conditioning, a swimming pool, and is within easy reach of St. Boniface Episcopal Church Labyrinth and Siesta Key Beach Playground.
Cottage On Siesta Key Beach - Siesta Key, FL
9.8 348 reviews

Cottage On Siesta Key Beach

cottage, Siesta Key
This charming cottage is located just a short walk from Siesta Key Beach, renowned as the #1 beach in the United States, and a short distance from the Point of Rocks. It's situated in a peaceful neighbourhood, just a short bus ride from Siesta Key Village. The cottage has excellent ratings for location, cleanliness and user experience.
The two-bedroom property sleeps up to five guests, comfortably offering a king-size bed in the master bedroom and twin beds in the second bedroom. Guests can enjoy a private pool, fishing dock, boat dock, and a Tiki Hut with grills, as well as a fully equipped kitchen, air conditioning, and internet access.
Stylish & Bright: Steps To Beach ~ Pool ~ Hot Tub! - Siesta Key, FL
10 1 review

Stylish & Bright: Steps To Beach ~ Pool ~ Hot Tub!

apartment, Siesta Key
This Siesta Key holiday let is located a mere 2-minute walk from Siesta Key Public Beach and a 13-minute walk from Siesta Key Beach Playground, offering convenient on-site parking for car-free exploration.
This 93 square meter apartment accommodates up to 10 guests and features a private heated swimming pool, hot tub, terrace, a fully equipped kitchen, and complimentary Wi-Fi, with the added convenience of an in-unit washer and dryer.

Frequently asked questions about holiday rentals in Siesta Key, FL

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Best Siesta Key, FL holiday rentals with a balcony

2nd Floor, Beach Access, Heated Pool, Tennis/pickleball, On Canal | Ready To Book! - Siesta Key, FL
10 7 reviews

2nd Floor, Beach Access, Heated Pool, Tennis/pickleball, On Canal | Ready To Book!

apartment, Siesta Key
This Siesta Key condo is ideally situated less than 1.6km from Crescent Beach and Siesta Key Beach, and 4km from Turtle Beach, offering easy access to Siesta Key's renowned sands.
This 80 square metre, two-bedroom, two-bathroom apartment sleeps four guests and boasts a fully equipped kitchen, private terrace, swimming pool, fitness centre, tennis court, and free Wi-Fi, alongside BBQ facilities and on-site parking.
The Beach Club At Siesta Key #106a Resort By Rva - Siesta Key, FL
9.0 80 reviews

The Beach Club At Siesta Key #106a Resort By Rva

apartment, Siesta Key
The Beach Club At Siesta Key #106a Resort By Rva is situated on Siesta Key, within a mile of Crescent Beach and Siesta Key Beach, offering easy access to the island's renowned white sand beaches. It's also within a 15-minute drive of Siesta Key Marina and Point of Rocks, perfect for exploring the area's natural beauty. The resort has consistently earned excellent ratings for its location, cleanliness and user experience.
This two-bedroom apartment comfortably accommodates up to six guests. The property offers a range of amenities, including a swimming pool, a jacuzzi, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.
Harbor Towers Yacht And Racquet Club On Siesta Key - Siesta Key, FL
8.0 9 reviews

Harbor Towers Yacht And Racquet Club On Siesta Key

apartment, Siesta Key
This Siesta Key apartment, a 16-minute walk from Siesta Key Beach and a 7-minute walk from Crescent Beach, offers easy access to two of the area's most beautiful beaches and is situated 18km from the John and Mable Ringling Museum of Art.
The 107-square-metre property features two bedrooms, two bathrooms, sleeps eleven guests, and boasts a fully equipped kitchen, private balcony with river views, plus resort amenities including a swimming pool, sauna, fitness centre, and tennis courts.
Steps To #1 Beach In America Siesta Beach! - Siesta Key, FL
9.6 81 reviews

Steps To #1 Beach In America Siesta Beach!

house, Siesta Key
This property is located on Siesta Key, just a 1.8 kilometre walk from the renowned Siesta Key Beach, the #1 beach in America, and is about 1.8 kilometres from Crescent Beach. It has excellent user, location and cleanliness ratings.
The two-bedroom, two-bathroom house can accommodate up to four guests. It has a fully equipped kitchen, a private balcony, a garden, a tennis court, free parking, and free Wi-Fi.

Best Siesta Key, FL holiday rentals with parking

Unwind Poolside + Walk To Beach! Sarasota Retreat - Siesta Key, FL
8.0 6 reviews

Unwind Poolside + Walk To Beach! Sarasota Retreat

apartment, Siesta Key
This 3-bedroom, 3-bathroom flat in Siesta Key's South Village is within walking distance of local eateries and public beach access, and is located 3.2 kilometres from Siesta Key Beach, 17.7 kilometres from St. Armands Circle, and 11.3 kilometres from the Mall at University Town Center.
This 117 square metre apartment accommodates up to six guests, offering a heated outdoor community pool, in-unit laundry, air conditioning, Wi-Fi, a fully equipped kitchen, and five Smart TVs, with pets welcome for an additional fee.
Private Patio, Walk To All! 5min- Siesta Keys Best Beach, 1min- Shopping Dining & Entertainment! - Siesta Key, FL
8.7 3 reviews

Private Patio, Walk To All! 5min- Siesta Keys Best Beach, 1min- Shopping Dining & Entertainment!

apartment, Siesta Key
This Siesta Key apartment is ideally located less than 0.8km from Crescent Beach and a one-minute walk from shops and restaurants.
The 46 square metre flat offers one bedroom, one bathroom, sleeps seven, and includes a fully equipped kitchen, private patio, free Wi-Fi, parking, and a washing machine; nearby attractions include Turtle Beach (1.9km), Marina Jack (12km), and the Ringling Museum (18km).
Amore Suite Siesta Sunset Bungalows ! Private Jacuzzi 6 Min From The Siesta Key! - Siesta Key, FL
10 2 reviews

Amore Suite Siesta Sunset Bungalows ! Private Jacuzzi 6 Min From The Siesta Key!

apartment, Siesta Key
This pet-friendly Siesta Key apartment rental is conveniently located a short drive (approx. 8km and 14km respectively) from Siesta Key Public Beach and Crescent Beach.
The one-bedroom, one-bathroom flat sleeps two guests and boasts a full kitchen, in-unit laundry, a private terrace, free Wi-Fi, a swimming pool, jacuzzi and garden access, perfect for a relaxing beach getaway.
Lulu's Cozy Beach Cottage #1 | 5 Min. Walk To Beach | Dog Friendly | Pool | $185 Free Activities! - Siesta Key, FL
9.8 22 reviews

Lulu's Cozy Beach Cottage #1 | 5 Min. Walk To Beach | Dog Friendly | Pool | $185 Free Activities!

apartment, Siesta Key
This Siesta Key apartment is centrally located, less than 1.6km from Point of Rocks and Crescent Beach, and within 3.2km of Siesta Key Beach and Turtle Beach.
This 83 square metre, three-bedroom, two-bathroom property sleeps six, boasting a fully equipped kitchen, private patio, swimming pool, tennis court, free Wi-Fi, and parking; barbecue facilities are also available within the smoke-free building.
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