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

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355 Best Villa Rentals in Siesta Key Village (Starting from $233)

Siesta Key Beachside Villas
Siesta Key Beachside Villas
Villa
Siesta Key Village, Siesta Key, Florida, USA
0.1k from Siesta Key Village 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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Village West in heart of Siesta
Village West in heart of Siesta
Villa
Siesta Key, FL, 34242, United States
0.1k from Siesta Key Village center

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

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$369
Average price / night
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Siesta Key Beach Resort and Suites
Siesta Key Beach Resort and Suites
Villa
Sarasota, FL, USA
0.4k from Siesta Key Village 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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100 Yds to Beach+2 Blocks to Siesta Key Village ; Heated Pool
100 Yds to Beach+2 Blocks to Siesta Key Village ; Heated Pool
Villa
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Dryer, Free Parking, Internet, Laundry, Living Area, Microwave, No Smoking, Pool

1 Bedroom4 Guests
New to Booking
$328
Average price / night
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Island House Beach Resort 10B
Island House Beach Resort 10B
Villa
Siesta Key Village, Siesta Key, Florida, USA
2.2k from Siesta Key Village 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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In the Heart of Siesta Key Village and Steps to the #1 Beach
In the Heart of Siesta Key Village and Steps to the #1 Beach
Villa
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

106 reviews

$386
Average price / night
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Island House Beach Resort 40B
Island House Beach Resort 40B
Villa
Siesta Key, FL, USA
2.2k from Siesta Key Village 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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Canal Lower-Gorgeous 3 bed 3 bath near SK Village
Canal Lower-Gorgeous 3 bed 3 bath near SK Village
Villa
Siesta Key, FL, 34242, United States
0.3k from Siesta Key Village center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

9.6

Exceptional

40 reviews

$937
Average price / night
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Casa Mar By Beachside Management
Casa Mar By Beachside Management
Villa
Sarasota, FL, USA
2.9k from Siesta Key Village 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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Luxury 2 bed & 2 bath Villa. Next to Siesta Key Village and beach  access 5.
Luxury 2 bed & 2 bath Villa. Next to Siesta Key Village and beach access 5.
Villa
Siesta Key, FL, 34242, United States
0.3k from Siesta Key Village center

AC, Balcony, Crib, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms5 Guests
10.0

Exceptional

13 reviews

$602
Average price / night
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Siesta Key Bay View Beach Access
Siesta Key Bay View Beach Access
Villa
Siesta Key, FL, USA
3.1k from Siesta Key Village 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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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
0.7k from Siesta Key Village 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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Beautiful property on Siesta Key
Beautiful property on Siesta Key
Villa
Siesta Key, FL, USA
3.1k from Siesta Key Village 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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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
1.9k from Siesta Key Village 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 V31 villa
Island House Beach Resort V31 villa
Villa
Siesta Key, FL, USA
3.3k from Siesta Key Village 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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Island House Beach Resort V10B
Island House Beach Resort V10B
Villa
Siesta Key, FL, 34242, United States
2.2k from Siesta Key Village 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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Condo 101
Condo 101
Villa
Sarasota, FL, USA
3.3k from Siesta Key Village center

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

1 Bedroom4 Guests
New to Booking
$662
Average price / night
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Island House Beach Resort V40A
Island House Beach Resort V40A
Villa
Siesta Key, FL, 34242, United States
2.2k from Siesta Key Village 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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Island House Beach Resort 1
Island House Beach Resort 1
Villa
Point O'Rocks, FL, USA
3.3k from Siesta Key Village center

Internet, Kitchen, Pool, Air Conditioner, Child Friendly

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$324
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
2.4k from Siesta Key Village 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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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
2.4k from Siesta Key Village 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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  Remodeled 1-bedroom villa, beach front, Jamaica Royale, Siesta Key
Remodeled 1-bedroom villa, beach front, Jamaica Royale, Siesta Key
Villa
Sarasota, FL, 34242, United States
2.5k from Siesta Key Village center

AC, Barbecue, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, Pool

1 Bedroom6 Guests
New to Booking
$358
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
2.5k from Siesta Key Village 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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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
2.5k from Siesta Key Village 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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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
2.5k from Siesta Key Village 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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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
2.6k from Siesta Key Village 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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Beachaven #8. Newly renovated. Best Beach. Siesta Key FL
Beachaven #8. Newly renovated. Best Beach. Siesta Key FL
Villa
Sarasota, FL, 34242, United States
2.6k from Siesta Key Village center

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

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$233
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 Village.

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Siesta Key Village Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 355 verified villa rentals in Siesta Key Village. 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 Village 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 Village 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 Village.

Yes, Siesta Key Village 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 Village 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 Village often include highly sought-after amenities such as View, Fireplace/Heating, and Ocean View. These features enhance comfort and convenience, making them especially popular among travelers visiting Siesta Key Village.

To discover top-rated villas in Siesta Key Village, 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.