Villa Rentals in Siesta Key Beach, FL: Compare 10+ Sites & Save

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354 Best Villa Rentals in Siesta Key Beach (Starting from $233)

Island House Beach Resort 10B
Island House Beach Resort 10B
Villa
Siesta Key Beach, Siesta Key, Florida, USA
0.8k from Siesta Key Beach center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
8.0

Good

1 reviews

$318
Average price / night
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Newly Renovated Family Home, Pool, Walk to Siesta Beach
Newly Renovated Family Home, Pool, Walk to Siesta Beach
Villa
Siesta Key, FL, 34242, United States
0.8k from Siesta Key Beach center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$425
Average price / night
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Island House Beach Resort 40B
Island House Beach Resort 40B
Villa
Siesta Key, FL, USA
0.8k from Siesta Key Beach center

Fireplace/Heating, Pool, Air Conditioner, Guest Services, Eco Friendly, Internet, Security/Safety

2 Bedrooms4 Guests
New to Booking
$405
Average price / night
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Island House Beach Resort V10B
Island House Beach Resort V10B
Villa
Siesta Key, FL, 34242, United States
0.8k from Siesta Key Beach center

AC, Arcade, Barbecue, Dryer, Heater, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
8.8

Fabulous

20 reviews

$476
Average price / night
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Casa Mar By Beachside Management
Casa Mar By Beachside Management
Villa
Sarasota, FL, USA
1.3k from Siesta Key Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms16 Guests
9.2

Superb

23 reviews

$317
Average price / night
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Island House Beach Resort V40A
Island House Beach Resort V40A
Villa
Siesta Key, FL, 34242, United States
0.8k from Siesta Key Beach center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$495
Average price / night
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Siesta Key Beach Resort and Suites
Siesta Key Beach Resort and Suites
Villa
Sarasota, FL, USA
1.4k from Siesta Key Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

50 Bedrooms44 Guests
8.3

Very Good

720 reviews

$368
Average price / night
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Jamaica Royale #11- Everything NEW, 3 Heated Pools, Right on the Beach!
Jamaica Royale #11- Everything NEW, 3 Heated Pools, Right on the Beach!
Villa
Siesta Key, FL, 34242, United States
0.8k from Siesta Key Beach center

AC, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
8.0

Good

7 reviews

$415
Average price / night
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Siesta Key Bay View Beach Access
Siesta Key Bay View Beach Access
Villa
Siesta Key, FL, USA
1.5k from Siesta Key Beach center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
7.8

Good

64 reviews

$360
Average price / night
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Jamaica Royale #40 - 3 Heated Pools on the Beach - One Ocean-Side!
Jamaica Royale #40 - 3 Heated Pools on the Beach - One Ocean-Side!
Villa
Siesta Key, FL, 34242, United States
0.8k from Siesta Key Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
10.0

Exceptional

11 reviews

$379
Average price / night
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Beautiful property on Siesta Key
Beautiful property on Siesta Key
Villa
Siesta Key, FL, USA
1.5k from Siesta Key Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

2 Bedrooms4 Guests
8.4

Very Good

51 reviews

$250
Average price / night
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Beachaven #8. Newly renovated. Best Beach. Siesta Key FL
Beachaven #8. Newly renovated. Best Beach. Siesta Key FL
Villa
Sarasota, FL, 34242, United States
0.9k from Siesta Key Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$233
Average price / night
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Island House Beach Resort V31 villa
Island House Beach Resort V31 villa
Villa
Siesta Key, FL, USA
1.6k from Siesta Key Beach center

Breakfast, Security/Safety, Air Conditioner, View, Pool, Ocean View, Fireplace

2 Bedrooms4 Guests
New to Booking
$259
Average price / night
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Completely remodeled villa next to famous Siesta Key Beach in Sarasota
Completely remodeled villa next to famous Siesta Key Beach in Sarasota
Villa
Siesta Key, FL, 34242, United States
0.9k from Siesta Key Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom5 Guests
9.2

Superb

5 reviews

$285
Average price / night
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Siesta Key Beachside Villas
Siesta Key Beachside Villas
Villa
Siesta Key Beach, Siesta Key, Florida, USA
1.6k from Siesta Key Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, 3-star, Lodgings, Vacation rentals

18 Bedrooms20 Guests
8.7

Fabulous

407 reviews

$1174
Average price / night
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Discover OUR BEST PRICES for 2026-Charming 2Bed/2Bath villa.\nInquire today!
Discover OUR BEST PRICES for 2026-Charming 2Bed/2Bath villa.\nInquire today!
Villa
Siesta key, FL, 34242, United States
1.0k from Siesta Key Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$261
Average price / night
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Island House Beach Resort 1
Island House Beach Resort 1
Villa
Point O'Rocks, FL, USA
1.6k from Siesta Key Beach center

Internet, Kitchen, Pool, Air Conditioner, Child Friendly

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$324
Average price / night
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Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Renovated
Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Renovated
Villa
Sarasota, FL, 34242, United States
1.0k from Siesta Key Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$412
Average price / night
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Island House Beach Resort 10A
Island House Beach Resort 10A
Villa
Siesta Key Beach, Siesta Key, Florida, USA
1.6k from Siesta Key Beach center

Internet, Air Conditioner, Guest Services, Fireplace, Pool, Security/Safety, Child Friendly

2 Bedrooms4 Guests
New to Booking
$292
Average price / night
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Siesta Key 3 Bedrm, 3½ bath Villa sleeps 8 with 2900sq ft
Siesta Key 3 Bedrm, 3½ bath Villa sleeps 8 with 2900sq ft
Villa
Siesta Key, FL, 34242, United States
1.0k from Siesta Key Beach center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Internet

3 Bedrooms8 Guests
10.0

Exceptional

22 reviews

$848
Average price / night
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58 Premium Plus - Casa Mar
58 Premium Plus - Casa Mar
Villa
Sarasota, FL, 34242, United States
1.1k from Siesta Key Beach center

AC, Barbecue, Free Parking, Microwave, No Smoking, TV

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$515
Average price / night
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44 Premium Plus - Sandy Toes & Seaside Bliss
44 Premium Plus - Sandy Toes & Seaside Bliss
Villa
Siesta Key, FL, 34242, United States
1.2k from Siesta Key Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Laundry, No Smoking, Pool

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$514
Average price / night
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40 Standard Plus, Beachful Bliss
40 Standard Plus, Beachful Bliss
Villa
Siesta Key, FL, 34242, United States
1.2k from Siesta Key Beach center

AC, Barbecue, Free Parking, Internet, Laundry, No Smoking, Pool, Tennis Court, TV

2 Bedrooms6 Guests
New to Booking
$525
Average price / night
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24 Premium - Romantic Siesta Key Delightful One-Bedroom Villa for Two
24 Premium - Romantic Siesta Key Delightful One-Bedroom Villa for Two
Villa
Siesta Key, FL, 34242, United States
1.2k from Siesta Key Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Laundry, No Smoking, Pool, Tennis Court

1 Bedroom2 Guests
10.0

Exceptional

3 reviews

$381
Average price / night
Check Availability
Newly renovated. Gulf-side condo. Your own private beach directly on Siesta Key.
Newly renovated. Gulf-side condo. Your own private beach directly on Siesta Key.
Villa
Siesta Key, FL, 34242, United States
1.2k from Siesta Key Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

15 reviews

$233
Average price / night
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Stay In Our Ground Floor Villa, Perfectly Located Between The Pool And The Bay.
Stay In Our Ground Floor Villa, Perfectly Located Between The Pool And The Bay.
Villa
Siesta Key, FL, 34242, United States
1.2k from Siesta Key Beach center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
8.0

Good

9 reviews

$396
Average price / night
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65 Premium- Island Vibes - Your Perfect One-Bedroom Villa in Siesta Key Awaits
65 Premium- Island Vibes - Your Perfect One-Bedroom Villa in Siesta Key Awaits
Villa
Siesta Key, FL, 34242, United States
1.3k from Siesta Key Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Laundry, No Smoking, Pool

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$342
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Villa Rentals in Siesta Key Beach.

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Siesta Key Beach Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 354 verified villa rentals in Siesta Key Beach. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Siesta Key Beach vary depending on the season, location, and amenities. Rates typically start from around $233 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Siesta Key Beach are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Siesta Key Beach.

Yes, Siesta Key Beach offers a wide range of villas ideal for group stays. Many properties include 2 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Siesta Key Beach villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Siesta Key Beach often include highly sought-after amenities such as Ocean View, View, and Pool. These features enhance comfort and convenience, making them especially popular among travelers visiting Siesta Key Beach.

To discover top-rated villas in Siesta Key Beach, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.