Apartment
10.0(168 Reviews)
2 Bedrooms
1 Bath
5 Guests
1200 ft²
Private Pool
Oceanfront
Hot Tub
Parking
US $320/Night
7 Nights - US $2,242
Siesta Key Holiday Homes
10.0
House
10.0(9 Reviews)
3 Bedrooms
3 Baths
10 Guests
1646.88 ft²
- Oceanfront
- Parking
Pool
Ocean View
US $1,761/Night
7 Nights - US $12,327
US $392/Night
7 Nights - US $2,747
Villa
10.0(113 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Oceanfront
- Parking
- Ocean View
Balcony/Terrace
US $379/Night
7 Nights - US $2,653
House
10.0(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
1915.98 ft²
- Parking
- Pool
Kitchen
Internet
US $302/Night
7 Nights - US $2,114
House
10.0(77 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $502/Night
7 Nights - US $3,515
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
1001.04 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $562/Night
7 Nights - US $3,934
House
10.0(70 Reviews)
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $243/Night
7 Nights - US $1,702
House
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
193.75 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $568/Night
7 Nights - US $3,976
Villa
10.0(51 Reviews)
2 Bedrooms
1 Bath
4 Guests
630 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $245/Night
7 Nights - US $1,717
Apartment
10.0(4 Reviews)
8 Bedrooms
8 Baths
22 Guests
1251.3 ft²
- Parking
View- Internet
Child Friendly
US $724/Night
7 Nights - US $5,068
House
10.0(49 Reviews)
2 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,038/Night
7 Nights - US $7,263
Why Choose Rent By Owner for your Siesta Key Holiday Homes?
What makes our Holiday Homes special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Siesta Key
How to Book Your Siesta Key Holiday Homes
What's our booking process?
Our platform allows you to browse a curated selection of holiday homes. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Holiday Homes Amenities
What amenities can you expect?
Our Holiday Homes are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Siesta Key, FL
Siesta Key Marina
Crescent Beach
St. Boniface Episcopal Church Labyrinth
Point of Rocks
Siesta Key Beach
Irma Beach
Shell Beach
Turtle Beach
Siesta Key Village
Aloha Kai
Bay Island
Bay Isle
Frequently Asked Questions About Siesta Key Holiday Rentals
1. What are the top Holiday Homes 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 Holiday Homes in Siesta Key:
- Stunning Siesta Key, . , Walk to Shell Beach, HEATED POOL 14 max
- Siesta Key private beach access
- Garage Parking, King beds-NO Bunks, Pool & Private Beach Access-No Crowds
- "CHATEAU du SOLEIL" SINGLE Family Home 1-1/2 Blocks to Beach Private Pool
- Siesta Key FamilyGetaway!
- 4-bedroom townhome with pool and steps to beach close to village
- Private back yard with heated pool. Pet friendly 3 bedroom house, close to beach
- Pool Volleyball-Gulf Views-Steps to Beach-Rooftop
- Steps to Beach/Pool w/Slide and Chipping Green
- Gulf Views/Steps to Beach/Resort Pool w/Slide/Spa
2. How many Holiday Homes are available in Siesta Key?
Currently, the total number of properties listed by RBO in 2026 is over 2868 in the Siesta Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Siesta Key.
More Rentals You May Like Near Siesta Key
Apartment
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
1205.56 ft²
- Oceanfront
- Parking
- Pool
Spa
US $281/Night
7 Nights - US $1,967
House
10.0(46 Reviews)
1 Bedroom
1 Bath
4 Guests
537 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $641/Night
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House
10.0(46 Reviews)
2 Bedrooms
2 Baths
6 Guests
2075 ft²
- Private Pool
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- Parking
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US $498/Night
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Villa
10.0(46 Reviews)
2 Bedrooms
1 Bath
4 Guests
630 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $246/Night
7 Nights - US $1,724
House
10.0(38 Reviews)
1 Bedroom
1 Bath
4 Guests
537 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $638/Night
7 Nights - US $4,469
Apartment
10.0(37 Reviews)
1 Bedroom
1 Bath
4 Guests
450 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $342/Night
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Apartment
10.0(35 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $599/Night
7 Nights - US $4,194
House
10.0(33 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $284/Night
7 Nights - US $1,989
House
10.0(32 Reviews)
1 Bedroom
1 Bath
4 Guests
960 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $207/Night
7 Nights - US $1,448
Apartment
10.0(31 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Oceanfront
- Parking
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- Ocean View
US $495/Night
7 Nights - US $3,463
Apartment
10.0(30 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $253/Night
7 Nights - US $1,773
Apartment
10.0(27 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $767/Night
7 Nights - US $5,366
