Estia Villas - Vacation Rentals in Siesta Key
Villa
9.0
(
20 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1000 ft²
-
Oceanfront -
Pool -
Ocean View -
Balcony/Terrace
US $390
/Night
7 Nights - $2,731
Villa
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
6 Guests
1001.04 ft²
-
Pool
-
Kitchen -
Air Conditioner -
Internet
US $324
/Night
7 Nights - $2,268
Villa
9.6
(
18 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1 ft²
-
Oceanfront
-
Pool
-
Ocean View
-
Balcony/Terrace
US $396
/Night
7 Nights - $2,769
Villa
9.6
(
63 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking -
Kitchen
-
Internet
-
Child Friendly
US $304
/Night
7 Nights - $2,128
Villa
9.6
(
20 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1000 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $390
/Night
7 Nights - $2,731
Villa
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
1248 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $292
/Night
7 Nights - $2,045
Villa
9.8
(
21 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1000 ft²
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $390
/Night
7 Nights - $2,731
See More Siesta Key Vacation Rentals
Luxury Places to Stay in Siesta Key
Over 5982+
Luxury Places to Stay in or Near Siesta Key
House
3 Bedrooms
4 Bathrooms
6 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
Unlock the Best Price
House
8 Bedrooms
6 Bathrooms
24 Guests
4014.94 ft²
-
Parking
-
View -
Internet
-
Pet Friendly
US $6,966
/Night
7 Nights - $48,760
US $6,470
/Night
7 Nights - $45,287
House
1 Bedroom
15 Bathrooms
37 Guests
8395.85 ft²
-
EV Charge Station -
Parking
-
Pool
-
Spa
US $6,447
/Night
7 Nights - $45,127
House
1 Bedroom
17 Bathrooms
41 Guests
8998.63 ft²
-
EV Charge Station
-
Parking
-
Pool
-
Spa
US $6,434
/Night
7 Nights - $45,037
House
10.0
(
2 Reviews
)
12 Bedrooms
14 Bathrooms
36 Guests
8000 ft²
-
Private Pool -
Oceanfront
-
Parking
-
Pool
US $6,163
/Night
7 Nights - $43,139
House
14 Bedrooms
15 Bathrooms
38 Guests
8000 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $5,878
/Night
7 Nights - $41,146
House
15 Bedrooms
17 Bathrooms
41 Guests
9000 ft²
-
Oceanfront
-
Hot Tub -
Parking
-
Pool
US $5,830
/Night
7 Nights - $40,807
See More Siesta Key Luxury Vacation Rentals
Find More Siesta Key Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Siesta Key
Over 4565+
Top-Rated Vacation Rentals with a Pool in or Near Siesta Key
Condo
10.0
(
218 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1400 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $280
/Night
7 Nights - $1,962
Cottage
10.0
(
201 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $492
/Night
7 Nights - $3,445
Condo
10.0
(
198 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1250 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $208
/Night
7 Nights - $1,456
Condo
10.0
(
178 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1400 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $226
/Night
7 Nights - $1,581
Condo
10.0
(
169 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1773 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $251
/Night
7 Nights - $1,760
Apartment
10.0
(
167 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1200 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $324
/Night
7 Nights - $2,268
Condo
10.0
(
154 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1224 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $426
/Night
7 Nights - $2,984
Condo
10.0
(
142 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
851 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $466
/Night
7 Nights - $3,264
Pet-Friendly Vacation Rentals in Siesta Key
Over 1054+
Pet-Friendly Vacation Rentals in or Near Siesta Key
Cottage
10.0
(
344 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
600 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $333
/Night
7 Nights - $2,331
House
10.0
(
8 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1915.98 ft²
-
Parking
-
Pool
-
Kitchen
-
Internet
US $302
/Night
7 Nights - $2,114
House
10.0
(
5 Reviews
)
1 Bedroom
1 Bathroom
-
Pool
-
Ocean View
-
Balcony/Terrace
-
View
US $2,529
/Night
7 Nights - $17,703
House
10.0
(
17 Reviews
)
6 Bedrooms
6 Bathrooms
20 Guests
2387 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $1,854
/Night
7 Nights - $12,975
House
9.6
(
67 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1671 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $1,072
/Night
7 Nights - $7,502
House
9.6
(
58 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2419 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $571
/Night
7 Nights - $3,999
House
9.2
(
21 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
1500 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $986
/Night
7 Nights - $6,905
Condo
9.8
(
25 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1072 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $179
/Night
7 Nights - $1,253
See More Pet-Friendly Vacation Rentals in Siesta Key on PetFriendly.io
Large Vacation Homes & Villas in Siesta Key
Over 1135+
Large Vacation Homes & Villas in or Near Siesta Key
House
9.8
(
46 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
3500 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $1,443
/Night
7 Nights - $10,102
Villa
2 Bedrooms
2 Bathrooms
6 Guests
1001.04 ft²
-
Pool
-
Kitchen
-
Air Conditioner
-
Internet
US $378
/Night
7 Nights - $2,646
House
9.8
(
53 Reviews
)
6 Bedrooms
6 Bathrooms
18 Guests
4100 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $1,596
/Night
7 Nights - $11,169
House
9.8
(
44 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
3349 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $1,573
/Night
7 Nights - $11,012
House
The Big Kahuna | SK Village, Pet Friendly, 2 Heated Pools, Elevator, Ping Pong Tables Steps to Beach
10.0
(
13 Reviews
)
8 Bedrooms
6 Bathrooms
24 Guests
4018 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $3,026
/Night
7 Nights - $21,181
House
9.2
(
39 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2264 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $521
/Night
7 Nights - $3,650
House
10.0
(
3 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
3250 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $821
/Night
7 Nights - $5,747
House
9.8
(
76 Reviews
)
8 Bedrooms
7 Bathrooms
23 Guests
3563 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $1,933
/Night
7 Nights - $13,528
See More Family Vacation Rentals in Siesta Key on FVR
Wheelchair Accessible Vacation Homes in Siesta Key
Over 1875+
Wheelchair Accessible Vacation Homes in or Near Siesta Key
Condo
10.0
(
22 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Kitchen
US $482
/Night
7 Nights - $3,372
US $173
/Night
7 Nights - $1,211
Apartment
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $392
/Night
7 Nights - $2,747
Condo
9.8
(
117 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1089 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $457
/Night
7 Nights - $3,201
Condo
9.6
(
43 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1090 ft²
-
Parking
-
Pool
-
Ocean View
-
View
US $275
/Night
7 Nights - $1,925
Condo
10.0
(
122 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
2000 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $370
/Night
7 Nights - $2,588
Condo
10.0
(
116 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1100 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $431
/Night
7 Nights - $3,020
Condo
9.8
(
47 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1600 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $553
/Night
7 Nights - $3,869
Siesta Key Vacation Rentals and Airbnb Places to Stay Under $200
Over 490+
Siesta Key Vacation Rentals and Airbnb Places to Stay Under $200
Condo
9.8
(
46 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
861 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $199
/Night
7 Nights - $1,396
House
9.2
(
4 Reviews
)
1 Bedroom
2 Bathrooms
6 Guests
-
Pool
-
Ocean View
-
View
-
Kitchen
US $185
/Night
7 Nights - $1,295
Apartment
9.4
(
5747 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $179
/Night
7 Nights - $1,251
Condo
9.8
(
101 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
780 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $193
/Night
7 Nights - $1,351
Condo
9.2
(
21 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
748 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $159
/Night
7 Nights - $1,114
Condo
9.4
(
56 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
788 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $178
/Night
7 Nights - $1,247
Condo
8.0
(
103 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1101 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $191
/Night
7 Nights - $1,334
Condo
9.2
(
40 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
900 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $194
/Night
7 Nights - $1,361
See More Siesta Key Vacation Rental Deals
Instantly Bookable Vacation Homes in Siesta Key
Over 3964+
Instantly Bookable Vacation Homes in or Near Siesta Key
New
House
9.2
(
38 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1202 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $453
/Night
7 Nights - $3,171
US $430
/Night
7 Nights - $3,008
Condo
9.8
(
182 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
730 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $310
/Night
7 Nights - $2,167
Condo
9.8
(
66 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
1000 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $256
/Night
7 Nights - $1,791
Apartment
9.6
(
139 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $310
/Night
7 Nights - $2,169
Condo
9.6
(
122 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
640 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $344
/Night
7 Nights - $2,411
House
9.2
(
97 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1500 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $295
/Night
7 Nights - $2,065
Condo
9.2
(
80 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
984 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $532
/Night
7 Nights - $3,727
About Siesta Key Vacation Rentals
With more than 536 Siesta Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Siesta Key.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Siesta Key, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Siesta Key. Places to stay near Siesta Key are 596.73 ft² on average, with prices averaging US $381 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Siesta Key with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Siesta Key
| Type | Count |
|---|---|
| Villas | 511 |
| Vacation Homes | 16 |
| Holiday Apartments | 9 |
Use these Quick Filters to Find a Vacation Rental in Siesta Key
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Siesta Key.
Weather in Siesta Key
View the weather forecast for Siesta Key before booking your Siesta Key Vacation Rentals to confirm your best time to go.
December - February
High 79°F Low 51°F
March - May
High 91°F Low 53°F
June - August
High 92°F Low 72°F
September - November
High 90°F Low 57°F
Top Attractions Around Siesta Key, FL
Estiavillas offers a large selection of top attractions around Siesta Key. Research things to do on your vacation before you visit Siesta Key.
Siesta Key Beach
Turtle Beach
Crescent Beach
Siesta Key Marina
Point of Rocks
Shell Beach
St. Boniface Episcopal Church Labyrinth
Bay Island
Irma Beach
Jim Neville Marine Preserve
Lido Beach
Venice Beach
St. Armands Circle
IMG Academy
Nokomis Beach
Coquina Beach
Sarasota Jungle Gardens
Mote Marine Laboratory & Aquarium
Sarasota Memorial Hospital
John and Mable Ringling Museum of Art
Other Places to Stay Near Siesta Key, FL
Siesta Key Marina
7,064 Properties
Crescent Beach
6,975 Properties
St. Boniface Episcopal Church Labyrinth
6,964 Properties
Point of Rocks
6,874 Properties
Siesta Key Beach
6,531 Properties
Irma Beach
5,863 Properties
Shell Beach
5,424 Properties
Siesta Key Village
3,689 Properties
Turtle Beach
3,684 Properties
Aloha Kai
99 Properties
Bay Island
44 Properties
Bay Isle
44 Properties
Complexes around Siesta Key, FL
Cs Sarasota
118 Properties
Beachcomber Longboat Key
68 Properties
Aloha Kai Apts
55 Properties
Cove
23 Properties
Anna Maria Island Beach
9 Properties
Runaway Bay Bradenton Beach
9 Properties
Anchorage Resort Beach Boat Dock
7 Properties
Crescent Arms
7 Properties
Crescent Beach
7 Properties
Harbor
5 Properties
Casa Blanca Villa
4 Properties
Siesta Dunes
4 Properties
Point Of Rocks
3 Properties
Beach Resort
2 Properties
Class The Anchorage
2 Properties
Siesta Key Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Siesta Key?
There are a lot of options in Siesta Key. If you plan on staying in the Siesta Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Siesta Key:
- In the Heart of Siesta Key Village and Steps to the #1 Beach
- Completely Remodeled- 150 Yards to Beach and Restaurants!
- Newly Remodeled-150 Yards to Beach and Restaurants!
- Island House Beach Resort V1
- 80 second walk to private quartz beach
- Newly renovated. Gulf-side condo. Your own private beach on Siesta Key.
- Luxury 2 bed & 2 bath Villa. Next to Siesta Key Village and beach access 5.
- Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach! Patio
- 2025 completely remodeled private villa, 7 min walk to beach, entertainment
- Island House Beach Resort V33
How many vacation rentals have private pools in Siesta Key?
There are 864 vacation rentals with private pools near Siesta Key. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Siesta Key are best for families?
If you are looking for a family-friendly vacation home in Siesta Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Siesta Key:
How many vacation rentals are available in Siesta Key?
Currently, the total number of properties listed in 2026 is over 536 in the Siesta Key area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Siesta Key.
