Holiday Homes in Siesta Key
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
1745 rentals in Siesta Key.
Beach Vacation rental
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Siesta Key Dreams Penthouse Studio (321) - Beach, Shopping, Dining, Entertainmen
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key Dreams 1BR (321) - Beach, Shopping, Dining, Entertainment! 100 steps
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key Bay Front Beauty
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key Dreams 2BR (321) - Beach, Shopping, Dining, Entertainment! 100 steps
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Village Studio: Private Patio, Village Living, 200 steps to Top Beach, No Ca
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Oceanside 603 1BR - Beach-front in the world-famous Siesta Key Village!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Paradise! Remodeled 2 bedroom 2 bathroom with incredible views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Big Orange 1BR (Sunset) - Heated Pool, Siesta Village, Beaches, Daiquiris, S
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Oceanview 603 3BR - Beach-front in the world-famous Siesta Key Village!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Best of both worlds! Fish in bay or go to beach!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Oceanview 603 Penthouse - Oceanview, in Village, 30ft to Beach Path!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Gertrude's Village House - in the Top Location on the Island, Private Patio
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key Dreams 1BR (325) - Beach, Shopping, Dining, Entertainment! 100 steps
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
ON THE BEACH Palm Bay club 5th floor with open lanai, sunsets and ocean views
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Big Orange 3BR (Flamingo)- Steps to the sand path of Siesta's Top Beach!
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Casa Van Lopik (Canal) - Large Bohemian with Tiki-Bar, Balconies, and Tropical P
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key Dreams Penthouse Studio (325) - Beach, Shopping, Dining, Entertainmen
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Newly renovated condo with premium features on Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Under the Palms 1BR - steps to the best beaches, shopping, dining, and entertain
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Big Orange 3BR (Manatee) Unwind in the heart of Siesta Beach!
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Top Rated Gulf Side, Steps from Beach, Great Amenities 2 pools, tennis, hot tub
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key, Private Crescent Beach 2/2 Getaway
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
*** NEW *** Beachside Wonder.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
As seen on
LUXURY HOUSE BY THE CANAL , Pets welcome ��.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Big Orange 1BR/1Bath - Heated Pool, Siesta Village, Beaches, Daiquiris, Seaf
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Dreams PH - OceanViews, Roof Deck, Private Beach Path, in Siesta Village!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Hoppy's Beach-View Siesta Key - Spacious 3BR,Beach/Ocean Views,Private Elevator
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Oceanfront/Beachfront Condo in Premier Complex - Y Building
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
As seen on
Village Breeze III - Heated Pool, Private Patio, Village and Beach!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
1 Bed Cottage, Parking Spot,Beach Access #7, Walk to Village 5 min, 2 AC UNITS!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Dreams 1- OceanViews, Roof Deck, Private Beach Path, in the Village!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key 2 BR 1BA Villa, less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
SIESTA KEY BEACH , ROMANTIC UNIT C
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key Jamaica Royale 71 Beachside
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
"Safe & Clean" Key West Suite , only 60 steps to the Siesta Key Public Beach -
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Siesta Key Voted #1 Beach Siesta Dunes 2 Bedroom Condo Beautiful Beach Book Now
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Under the Palms 3BR - Private pool, Seafood, Steps to the beach and village!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Private Beach Front Complex w/3 pools, Steps to the Beach, WiFi Incl
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
"Safe & Clean" - Hibiscus Suite only 60 steps to the Siesta Key Public Beach -
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Showing results 1-50 of 1,745
Frequently Asked Questions about Siesta Key
- Yes, here are some popular holiday rentals in Siesta Key that have a pool:
- Beach Vacation rental
- Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key
- Best of both worlds! Fish in bay or go to beach!
- Yes, here are some popular holiday rentals in Siesta Key that have internet access:
- Beach Vacation rental
- Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key
- Siesta Key Dreams Penthouse Studio (321) - Beach, Shopping, Dining, Entertainmen
- The best pet friendly rentals in Siesta Key are:
- Siesta Key Dreams Penthouse Studio (321) - Beach, Shopping, Dining, Entertainmen
- Siesta Key Dreams 1BR (321) - Beach, Shopping, Dining, Entertainment! 100 steps
- Siesta Key Dreams 2BR (321) - Beach, Shopping, Dining, Entertainment! 100 steps
- Some of the most popular kid friendly rentals in Siesta Key are:
- Beach Vacation rental
- Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key
- Siesta Key Dreams Penthouse Studio (321) - Beach, Shopping, Dining, Entertainmen