Welcome to Siesta Key, a gem in Florida that shines with possibilities. With 3,623 villas to choose from, your perfect vacation is just a click away.

From cozy to lavish, Siesta Key offers a wide range of villas to suit your budget and style. With prices starting from $39 and going up to $22,628, you’re spoilt for choice with amenities such as Internet / Wifi.

Top Features: Internet / Wifi, Kitchen or Kitchenette, Air conditioner, Parking and Pool

Local Highlights: Mote Marine Laboratory & Aquarium, The John and Mable Ringling Museum of Art, Bayfront Park, South Jetty Beach and Robinson Preserve

Don't miss out on the beauty of Siesta Key. Book your villas now and experience the best of Florida.

Top villas in Siesta Key

Property building, Day, Garden, View (from property/room), Garden view
4.0
Good(61 Reviews)
Derby Bay View
Villa
 in Siesta Key
Garden · Pool · Kitchen or Kitchenette

This inviting Villa in Siesta Key can fit your needs for many types of vacations, at $242 per night.

$$$$
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Property view
4.3
Excellent(40 Reviews)
Beautiful property on Siesta Key
Villa
 in Siesta Key
Garden · Pool · Kitchen or Kitchenette
Most favorited

Villa in Siesta Key, for $244 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Bedroom
4.1
Excellent(1,045 Reviews)
Siesta Key Beach Resort and Suites
Villa
 in Sarasota
Garden · Pool · Kitchen or Kitchenette
Most favorited

Experience vacation in Siesta Key with our Villa, Siesta Key Beach Resort and Suites. Enjoy amenities such as Air conditioner, Internet / Wifi and Smoking allowed, and more.

$$$$
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Living room
4.2
Excellent(506 Reviews)
Siesta Key Beachside Villas
Villa
 in Sarasota
Garden · Pool · Kitchen or Kitchenette
Most favorited

Soak up the beauty of Siesta Key in our Villa, Siesta Key Beachside Villas. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Kitchen or kitchenette, oven, stove, toaster
4.1
Excellent(43 Reviews)
Sea Club II
Villa
 in Siesta Key
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a memorable stay in Siesta Key? Our Villa might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Property view
Happy Dolphin Siesta Key
Villa
 in Siesta Key
Garden · Pool · Kitchen or Kitchenette

This Villa in Siesta Key, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Villa, 2 Bedrooms | Beach
Island House Beach Resort V18 by RedAwning
Villa
 in Siesta Key
Pool · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Siesta Key? This Villa offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
5.0
Outstanding(86 Reviews)
In the Heart of Siesta Key Village and Steps to the #1 Beach
Villa
 in Siesta Key
4 guests · 2 bedrooms · 1 bath
Pool · Pets allowed · Kitchen or Kitchenette

The best choice in Siesta Key for Villa, for $443 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Villa, 2 Bedrooms | Beach
Island House Beach Resort V18 by RedAwning
Villa
 in Siesta Key
2 guests
Pool · Kitchen or Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Siesta Key, at $298 per night for your next great vacation.

$$$$
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Property view
Discover the beauty of Siesta Key at Siesta Villa Whispering Palms
Villa
 in Siesta Key
Garden · Kitchen or Kitchenette · Air conditioner

Enjoy the best of Siesta Key in our Villa, Discover the beauty of Siesta Key at Siesta Villa Whispering Palms. A stunning property with amenities including Air conditioner, Dishwasher and Laundry, and more.

$$$$
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House (Canopy Cottage on Siesta Key) | Exterior
Canopy Cottage on Siesta Key
Villa
 in Siesta Key
2 guests
Pool · Pets allowed · Kitchen or Kitchenette

This Villa for $494 in Siesta Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.0
Good(4 Reviews)
Boutique Chic Villa. Steps From Pool, Pier, & Beach. Find Your Vacation Here.
Villa
 in Siesta Key
Garden · Kitchen or Kitchenette · Air conditioner

Soak up the beauty of Siesta Key in our Villa, Boutique Chic Villa. Steps From Pool, Pier, & Beach. Find Your Vacation Here.. With a range of amenities such as Air conditioner, Dishwasher and Laundry, you'll feel right at home.

$$$$
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Villas with internet & wifi in Siesta Key

Beach nearby, sun loungers, beach towels
4.9
Outstanding(82 Reviews)
Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.
Villa
 in Sarasota
6 guests · 2 bedrooms · 1 bath
Pets allowed · Kitchen or Kitchenette · Air conditioner

This attractive Villa in Siesta Key, $320 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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On the beach, sun loungers, beach towels
4.8
Outstanding(74 Reviews)
Newly Remodeled Luxury Beach Villa! Nearest Stand-Alone Villa on Siesta Key!
Villa
 in Sarasota
6 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Are you ready to indulge in a relaxing getaway? Our Villa in Siesta Key has everything you need for a rejuvenating stay. Treat yourself to Newly Remodeled Luxury Beach Villa! Nearest Stand-Alone Villa on Siesta Key!'s exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
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Aerial view
4.8
Outstanding(76 Reviews)
New 3 BR Mediterranean Villa Very Close To Siesta Key - Pool, Jacuzzi, Lake, BBQ
Villa
 in Sarasota
10 guests · 3 bedrooms · 2 baths
Garden · Pool · Pets allowed

Indulge in a peaceful retreat at New 3 BR Mediterranean Villa Very Close To Siesta Key - Pool, Jacuzzi, Lake, BBQ, our elegant Villa in Siesta Key. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Outdoor pool, a heated pool
4.6
Outstanding(89 Reviews)
“MOONMIST” Siesta Key villa with private hot tub in a 'jungle' setting
Villa
 in Sarasota
5 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Experience the best of Siesta Key with this Villa available for $205. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Terrace/patio
4.9
Outstanding(61 Reviews)
Spacious Villa with Lush Tropical Garden Very Close to Siesta Key!
Villa
 in Sarasota
4 guests · 2 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

When traveling to Siesta Key, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $183 per night.

$$$$
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Interior
4.2
Excellent(87 Reviews)
Unique private Canal home w/pool- walk to Village. Quiet Hours Observed
Castle / Palace
 in Sarasota
12 guests · 5 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Siesta Key with a stay at Unique private Canal home w/pool- walk to Village. Quiet Hours Observed, a top rated Castle / Palace with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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House (Canopy Cottage on Siesta Key) | Exterior
Canopy Cottage on Siesta Key
Villa
 in Siesta Key
Pool · Pets allowed · Kitchen or Kitchenette

Soak up the beauty of Siesta Key in our Villa, Canopy Cottage on Siesta Key. With a range of amenities such as Internet / Wifi, Laundry and Pets allowed, you'll feel right at home.

$$$$
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Outdoor pool, a heated pool
4.8
Outstanding(51 Reviews)
Beautifully Updated Villa Directly on Crescent Beach
Villa
 in Siesta Key
6 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Villa in Siesta Key, for $303 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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On the beach
4.8
Outstanding(41 Reviews)
RENOVATED Villa Beachside, Siesta Key private beach access 2br/2ba
Villa
 in Siesta Key
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

The best choice in Siesta Key for Villa, for $366 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Outdoor dining
4.6
Outstanding(39 Reviews)
Island House Beach Resort V7
Villa
 in Siesta Key
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Villa in Siesta Key, for $444 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Beach nearby
4.9
Outstanding(33 Reviews)
Island House Beach Resort V35
Villa
 in Siesta Key
4 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

This attractive Villa in Siesta Key, $345 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Outdoor dining
4.7
Outstanding(33 Reviews)
Island House Beach Resort V39
Villa
 in Siesta Key
6 guests · 3 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at Island House Beach Resort V39, our elegant Villa in Siesta Key. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Beach nearby
4.8
Outstanding(22 Reviews)
Island House Beach Resort V25
Villa
 in Siesta Key
6 guests · 3 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Experience the best of Siesta Key with this Villa available for $452. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Outdoor dining
4.5
Excellent(29 Reviews)
Island House Beach Resort V6
Villa
 in Siesta Key
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Siesta Key? This Villa offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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