Welcome to Siesta Key, a gem in Florida that shines with possibilities. With 3,281 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 $69 and going up to $20,000, you’re spoilt for choice with amenities such as Air conditioner.

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

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 view
5.0
Outstanding(83 Reviews)
Villa
 in Siesta Key
In the Heart of Siesta Key Village and Steps to the #1 Beach
4 guests · 2 bedrooms · 1 bath
Pool · Pets allowed · Kitchen / Kitchenette

The best choice in Siesta Key for Villa, for $315 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.0
Good(61 Reviews)
Villa
 in Siesta Key
Siesta Key Bay View
Garden · Pool · Kitchen / Kitchenette

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

$$$$
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Flooring
5.0
Outstanding(27 Reviews)
Villa
 in Siesta Key
Luxury Beach Villa with Stunning Gulf Views
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Looking to create some memories in Siesta Key? Look no further than our Villa, Island House Beach Resort V5. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property view
4.3
Excellent(34 Reviews)
Villa
 in Siesta Key
Beautiful property on Siesta Key
Garden · Pool · Kitchen / 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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Property view
4.1
Excellent(1,142 Reviews)
Villa
 in Sarasota
Siesta Key Beach Resort and Suites
Garden · Pool · Pets allowed
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 Pets allowed, and more.

$$$$
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Furniture
5.0
Outstanding(24 Reviews)
Villa
 in Siesta Key
Beachfront Villa with Gulf Views in Siesta Key
5 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner
Top rated

Looking for a Villa in Siesta Key, this Villa for $422 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Beach nearby, sun loungers, beach towels
4.9
Outstanding(76 Reviews)
Villa
 in Sarasota
Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.
6 guests · 2 bedrooms · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

This attractive Villa in Siesta Key, $227 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)
Villa
 in Sarasota
Newly Remodeled Luxury Beach Villa! Nearest Stand-Alone Villa on Siesta Key!
6 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / 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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Property view
4.8
Outstanding(76 Reviews)
Villa
 in Sarasota
New 3 BR Mediterranean Villa Very Close To Siesta Key - Pool, Jacuzzi, Lake, BBQ
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(86 Reviews)
Villa
 in Sarasota
“MOONMIST” Siesta Key villa with private hot tub in a 'jungle' setting
5 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Experience the best of Siesta Key with this Villa available for $163. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property grounds
4.9
Outstanding(61 Reviews)
Villa
 in Sarasota
Spacious Villa with Lush Tropical Garden Very Close to Siesta Key!
4 guests · 2 bedrooms · 2 baths
Garden · Kitchen / 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 $200 per night.

$$$$
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Outdoor pool, a heated pool
4.8
Outstanding(49 Reviews)
Villa
 in Siesta Key
Beautifully Updated Villa Directly on Crescent Beach
6 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Villa in Siesta Key, for $272 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Vacation rentals with air conditioning in Siesta Key

Property view
4.2
Excellent(45 Reviews)
Villa
 in Siesta Key
Sea Club II
Pool · Air conditioner · TV

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

$$$$
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Room
4.8
Outstanding(24 Reviews)
Villa
 in Siesta Key
Siesta Key Villa with Gulf Views and Pool
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

The best choice in Siesta Key for Villa, for $422 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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View from property
4.2
Excellent(84 Reviews)
Castle / Palace
 in Sarasota
Unique private Canal home w/pool- walk to Village. Quiet Hours Observed
12 guests · 5 bedrooms · 5 baths
Garden · Pool · Kitchen / 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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On the beach
4.8
Outstanding(34 Reviews)
Villa
 in Siesta Key
RENOVATED Villa Beachside, Siesta Key private beach access 2br/2ba
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

The best choice in Siesta Key for Villa, for $260 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Aerial view
4.9
Outstanding(31 Reviews)
Villa
 in Siesta Key
Island House Beach Resort V35
4 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

This attractive Villa in Siesta Key, $272 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property grounds
4.6
Outstanding(37 Reviews)
Villa
 in Siesta Key
Island House Beach Resort V7
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Villa in Siesta Key, for $290 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.2
Excellent(522 Reviews)
Villa
 in Sarasota
Siesta Key Beachside Villas
Garden · Pool · Pets allowed
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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Living Room
4.8
Outstanding(22 Reviews)
Villa
 in Siesta Key
Luxury Villa Steps from Gulf, Siesta Key Beach Resort
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Experience vacation in Siesta Key with our Villa, Island House Beach Resort V28. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property grounds
4.9
Outstanding(29 Reviews)
Villa
 in Siesta Key
Island House Beach Resort V5
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

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

$$$$
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Property grounds
4.7
Outstanding(30 Reviews)
Villa
 in Siesta Key
Island House Beach Resort V39
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / 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, Internet / Wifi and Laundry, and more.

$$$$
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Property grounds
4.5
Excellent(27 Reviews)
Villa
 in Siesta Key
Island House Beach Resort V13
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Experience the best of Siesta Key with this Villa available for $283. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property grounds
4.5
Excellent(28 Reviews)
Villa
 in Siesta Key
Island House Beach Resort V6
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / 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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