House
10.0(49 Reviews)
2 Bedrooms
8 Guests
Oceanfront
Parking
Ocean View
Balcony/Terrace
R16,754/Night
7 Nights - R117,272
Siesta Key, FL Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Siesta Key
10.0
House
10.0(9 Reviews)
3 Bedrooms
10 Guests
- Oceanfront
Hot Tub- Parking
Pool
R29,260/Night
7 Nights - R204,819
Villa
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
R5,604/Night
7 Nights - R39,229
Condo
10.0(48 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R5,103/Night
7 Nights - R35,723
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
Internet
Pet Friendly
R5,018/Night
7 Nights - R35,125
House
10.0(46 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
R10,708/Night
7 Nights - R74,952
Condo
10.0(43 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R6,538/Night
7 Nights - R45,776
Condo
10.0(42 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R4,683/Night
7 Nights - R32,782
Condo
10.0(40 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R3,828/Night
7 Nights - R26,801
Luxury Holiday Rentals in Siesta Key
Over 6358+ Luxury Holiday Rentals in or Near Siesta Key
House
3 Bedrooms
6 Guests
- Kitchen
Air Conditioner- Internet
Child Friendly
Unlock the Best Price
R115,738/Night
7 Nights - R810,170
R106,902/Night
7 Nights - R748,311
House
12 Bedrooms
35 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R99,024/Night
7 Nights - R693,164
House
15 Bedrooms
41 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
R96,498/Night
7 Nights - R675,485
House
14 Bedrooms
38 Guests
Private Pool- Parking
- Pool
- Ocean View
R90,896/Night
7 Nights - R636,272
House
10.0(3 Reviews)
7 Bedrooms
20 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
R90,829/Night
7 Nights - R635,807
House
13 Bedrooms
37 Guests
- Private Pool
- Parking
- Pool
- Ocean View
R90,128/Night
7 Nights - R630,889
R89,408/Night
7 Nights - R625,855
Top-Rated Holiday Rentals with a Pool in Siesta Key
Over 4917+ The Best Private Villas and Holiday Rentals in Siesta Key with a Pool
Condo
10.0(222 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R4,031/Night
7 Nights - R28,213
Cottage
10.0(211 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R8,177/Night
7 Nights - R57,240
Condo
10.0(202 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
R2,985/Night
7 Nights - R20,886
Condo
10.0(182 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R6,373/Night
7 Nights - R44,613
Condo
10.0(178 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R4,930/Night
7 Nights - R34,510
Condo
10.0(174 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R3,482/Night
7 Nights - R24,375
Condo
10.0(172 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R4,650/Night
7 Nights - R32,550
Apartment
10.0(170 Reviews)
2 Bedrooms
5 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R5,685/Night
7 Nights - R39,794
Condo
10.0(160 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
R8,048/Night
7 Nights - R56,326
Pet-Friendly Holiday Rentals in Siesta Key
Over 1094+ Pet-Friendly Holiday Rentals in or Near Siesta Key
House
10.0(38 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R11,528/Night
7 Nights - R80,701
House
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
R9,122/Night
7 Nights - R63,853
House
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R4,731/Night
7 Nights - R33,115
Condo
10.0(37 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R5,443/Night
7 Nights - R38,099
R16,723/Night
7 Nights - R117,056
House
10.0(34 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R6,068/Night
7 Nights - R42,469
Cottage
10.0(30 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R5,533/Night
7 Nights - R38,731
House
10.0(27 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R10,658/Night
7 Nights - R74,603
Condo
10.0(13 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R7,732/Night
7 Nights - R54,133
Large Holiday Rentals and Private Villas in Siesta Key
Over 1198+ Large Holiday Rentals and Private Villas in or Near Siesta Key
Villa
10.0(20 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R4,804/Night
7 Nights - R33,630
Apartment
10.0(4 Reviews)
8 Bedrooms
22 Guests
- Parking
- Pool
- Internet
- Child Friendly
R12,030/Night
7 Nights - R84,207
Villa
10.0(16 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
R7,859/Night
7 Nights - R55,014
Villa
10.0(3 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- View
- Air Conditioner
R4,353/Night
7 Nights - R30,473
Villa
10.0(15 Reviews)
2 Bedrooms
7 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R4,419/Night
7 Nights - R30,938
Villa
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R3,845/Night
7 Nights - R26,917
Villa
10.0(9 Reviews)
2 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
R7,619/Night
7 Nights - R53,336
Villa
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R7,680/Night
7 Nights - R53,751
Wheelchair Accessible Holiday Homes in Siesta Key
Over 2078+ Wheelchair Accessible Holiday Homes in or Near Siesta Key
R4,431/Night
7 Nights - R31,021
Apartment
10.0(1 Review)
4 Bedrooms
13 Guests
- Parking
- Pool
- View
- Air Conditioner
R29,539/Night
7 Nights - R206,779
R6,521/Night
7 Nights - R45,643
Condo
10.0(27 Reviews)
2 Bedrooms
5 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
R7,670/Night
7 Nights - R53,685
Apartment
10.0(1 Review)
3 Bedrooms
10 Guests
- Parking
- View
- Air Conditioner
- Internet
R20,485/Night
7 Nights - R143,391
Condo
10.0(26 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R11,170/Night
7 Nights - R78,192
Condo
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R5,902/Night
7 Nights - R41,323
Condo
10.0(25 Reviews)
1 Bedroom
6 Guests
- Parking
- View
- Kitchen
- Air Conditioner
R4,458/Night
7 Nights - R31,204
Condo
10.0(23 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R7,119/Night
7 Nights - R49,830
Siesta Key Private Villas and Holiday Homes Under $200
Over 509+ Siesta Key Private Villas and Holiday Homes Under $200
Condo
10.0(10 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R3,102/Night
7 Nights - R21,716
House
10.0(1 Review)
2 Bedrooms
6 Guests
Private Beach- Hot Tub
- Parking
- Pool
R3,223/Night
7 Nights - R22,564
Apartment
9.4(5968 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R2,820/Night
7 Nights - R19,739
Condo
10.0(9 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
Spa- Ocean View
R2,637/Night
7 Nights - R18,460
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Pool
- View
- Air Conditioner
- Internet
R3,190/Night
7 Nights - R22,331
Condo
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R3,241/Night
7 Nights - R22,680
House
10.0(5 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R2,863/Night
7 Nights - R20,038
Condo
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R2,985/Night
7 Nights - R20,886
Condo
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- View
R3,317/Night
7 Nights - R23,212
Instantly Bookable Holiday Homes in Siesta Key
Over 4289+ Instantly Bookable Holiday Homes in or Near Siesta Key
Apartment
10.0(37 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R5,279/Night
7 Nights - R36,953
Apartment
1 Bedroom
3 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R3,933/Night
7 Nights - R27,532
House
10.0(35 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
R9,595/Night
7 Nights - R67,160
Condo
10.0(31 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R3,491/Night
7 Nights - R24,441
Apartment
10.0(24 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R5,412/Night
7 Nights - R37,883
Apartment
10.0(24 Reviews)
1 Bedroom
3 Guests
- Parking
- Pool
- Ocean View
- View
R4,340/Night
7 Nights - R30,390
Condo
10.0(23 Reviews)
2 Bedrooms
5 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
R10,157/Night
7 Nights - R71,098
Condo
10.0(23 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R7,318/Night
7 Nights - R51,225
Condo
10.0(22 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R7,911/Night
7 Nights - R55,379
Book a Last Minute Place to Stay in Siesta Key
About Casai's Private Villas and Holiday Rentals in Siesta Key
Discover more than 6367 vacation rentals available in Siesta Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Siesta Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Siesta Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Siesta Key. On average, places to stay near Siesta Key offer 975.27 ft², with nightly prices averaging R8,596.
With Casai, finding and comparing holiday rentals in Siesta Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Siesta Key, FL
There are 6367 Siesta Key, FL Holiday Rentals
- Prices for a holiday home in Siesta Key start at R1,529
- Top rated vacation home in Siesta Key is Across The Street From #1 Beach
- Most popular short term in Siesta Key is Tropical Beach Resorts
- Cheapest place to stay in Siesta Key is Peppertree Perfection
- Most expensive holiday rental in Siesta Key is Luxury Siesta Key Wellness Retreat. 5-10 min walk to Siesta Beach and Village
Recently Booked Holiday Rentals in Siesta Key
- Beachfront home with private access to Siesta Key beach and walk to town!
- Private Heated Pool - 100 Steps to Beach Access - 5-min walk to Siesta Key Village
- The Salty Palm is a cozy 2-bedroom Villa in peaceful Sarasota on Crescent Beach
- Siesta Key Gulf Front Condo
- 323 Canal Rd - Siesta Key Village Condo
Frequently Asked Questions About Siesta Key?
What are the top holiday rentals in Siesta Key?
With numerous options available in Siesta Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Siesta Key:
- Across The Street From #1 Beach
- AJ's Bayside Treasure - Outstanding Waterfront Views & Private Beach Access!
- The Inn On Siesta Key
- On Siesta Key Beach, View, pool, 2 Bed 2 Ba, plus pull out Queen,
- GULF SIDE - Peaceful Private Condo, 2BR/2BA, Siesta Key Jamaica Royale #100
- 🦩Book Me Baby! Bayview Beauty at Siesta Key 🦩
- Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach
- Updated Beachfront Rental, Steps to the Gulf & a Relaxing Private Tiki Hut
- Steps to#1 rated Beach in USA Spacious2+2Condo,pool,garageTranquil Setting
- Walk To Siesta Village And Beach/Private Heated Pool & Hot Tub
How many holiday rentals have private pools in Siesta Key?
Discover a selection of holiday rentals with private pools near Siesta Key with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Siesta Key are best for families?
If you're searching for a family-friendly holiday home in Siesta Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Siesta Key:
How many Casai.co.za holiday rentals are available in Siesta Key?
As of 2026, Casai boasts over 6367 properties listed in the Siesta Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Siesta Key.
Nearby Neighborhood (4)
| Neighborhood | Property Count |
|---|---|
| Siesta Key Village Vacation Rentals in Sarasota, Florida | 3974 |
| South Sarasota Vacation Rentals in Sarasota, Florida | 123 |
| Aloha Kai Vacation Rentals in Sarasota, Florida | 101 |
| Bay Isle Vacation Rentals in Sarasota, Florida | 43 |
