Siesta Key, Florida

Vacation Rentals in Siesta Key, Florida

Discover 936 vacation rental properties in Siesta Key. From 1 to 13 bedrooms. Average $259/night. 100% have pools.

936 verified listings Book securely on VRBO Prices updated March 2026

936 properties available

Across The Street From #1 Beach

Across The Street From #1 Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$220/night
View Details → Book on VRBO
☀️ Beachfront Penthouse - Views! Beach & Pool Open! Wifi, Screened Lanai, CLEAN

☀️ Beachfront Penthouse - Views! Beach & Pool Open! Wifi, Screened Lanai, CLEAN

2 beds 2 baths
PoolA/CWiFiBalcony
$191/night
View Details → Book on VRBO
"Safe & Clean" - Hibiscus Suite only 60 steps to the Siesta Key Public Beach -

"Safe & Clean" - Hibiscus Suite only 60 steps to the Siesta Key Public Beach -

1 bed 1 bath
PoolA/CWiFiBalcony
$296/night
View Details → Book on VRBO
Charming Suite w/ Shared Pool, High-Speed WiFi - Steps to the Beach

Charming Suite w/ Shared Pool, High-Speed WiFi - Steps to the Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$174/night
View Details → Book on VRBO
Newly renovated. Gulf-side condo. Your own private beach directly on Siesta Key.

Newly renovated. Gulf-side condo. Your own private beach directly on Siesta Key.

1 bed 1 bath
PoolA/CWiFiBalcony
$156/night
View Details → Book on VRBO
Directly on Siesta Key Beach with a short walk to the Village

Directly on Siesta Key Beach with a short walk to the Village

2 beds 2 baths
PoolA/CWiFiBalcony
$232/night
View Details → Book on VRBO
Just Another Day in Paradise

Just Another Day in Paradise

2 beds 2 baths
PoolA/CWiFiBalcony
$306/night
View Details → Book on VRBO
Steps to the ⭐ Beach, Short Walk to the Village

Steps to the ⭐ Beach, Short Walk to the Village

2 beds 2 baths
PoolA/CWiFiBalcony
$163/night
View Details → Book on VRBO
Casa Mar - 50- Ground floor unit in Gulf side Complex

Casa Mar - 50- Ground floor unit in Gulf side Complex

1 bath
PoolA/CWiFiBalcony
$133/night
View Details → Book on VRBO
Walk to Beach, Updated Condo, Private Patio and Grill

Walk to Beach, Updated Condo, Private Patio and Grill

1 bed 1 bath
PoolA/CWiFiBalcony
$192/night
View Details → Book on VRBO
5th Floor Siesta Key Condo Across From Pristine Sand & Blue Waters 2bd/2b Views

5th Floor Siesta Key Condo Across From Pristine Sand & Blue Waters 2bd/2b Views

2 beds 2 baths
PoolA/CWiFiBalcony
$193/night
View Details → Book on VRBO
Waterfront Beach House- Pool - Kayaks - Bikes - Boat Ramp

Waterfront Beach House- Pool - Kayaks - Bikes - Boat Ramp

2 beds 2 baths
PoolA/CWiFiBalcony
$286/night
View Details → Book on VRBO
Condo located on the best beach in the United States

Condo located on the best beach in the United States

2 beds 2 baths
PoolA/CWiFiBalcony
$246/night
View Details → Book on VRBO
1 Bed Cottage, Parking Spot,Beach Access #7, Walk to Village 5 min, 2 AC UNITS!

1 Bed Cottage, Parking Spot,Beach Access #7, Walk to Village 5 min, 2 AC UNITS!

1 bed 1 bath
PoolA/CWiFiBalcony
$229/night
View Details → Book on VRBO
Private Patio, Walk to All, 2min- Siesta Keys Best Beach, 1min- Dining & Entertainment of Village!

Private Patio, Walk to All, 2min- Siesta Keys Best Beach, 1min- Dining & Entertainment of Village!

1 bed 1 bath
PoolA/CWiFiBalcony
$182/night
View Details → Book on VRBO
Beachside Vacation Rental Condo on Siesta Key with Pool Access

Beachside Vacation Rental Condo on Siesta Key with Pool Access

2 beds 1 bath
PoolA/CWiFiBalcony
$154/night
View Details → Book on VRBO
Beach Front condo at Jamaica Royale

Beach Front condo at Jamaica Royale

1 bed 1 bath
PoolA/CWiFiBalcony
$160/night
View Details → Book on VRBO
Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$216/night
View Details → Book on VRBO
Direct Siesta Key Beachfront condo!

Direct Siesta Key Beachfront condo!

2 beds 2 baths
PoolA/CWiFiBalcony
$274/night
View Details → Book on VRBO
Rent rebates: seniors 65+, active military or1st responders; May to Dec 7+ days

Rent rebates: seniors 65+, active military or1st responders; May to Dec 7+ days

2 beds 1 bath
PoolA/CWiFiBalcony
$108/night
View Details → Book on VRBO
2 BR/2 BA Condo on Siesta Key

2 BR/2 BA Condo on Siesta Key

2 beds 2 baths
PoolA/CWiFiBalcony
$352/night
View Details → Book on VRBO
Spectacular Beach View! Right on Beach! Views from all rooms! Paradise!

Spectacular Beach View! Right on Beach! Views from all rooms! Paradise!

2 beds 2 baths
PoolA/CWiFiBalcony
$251/night
View Details → Book on VRBO
Corner unit, water views, boat access, remodeled, elevator building, no pets

Corner unit, water views, boat access, remodeled, elevator building, no pets

2 beds 2 baths
PoolA/CWiFiBalcony
$166/night
View Details → Book on VRBO
"Safe & Clean" Hide-A-Way Suite, only 60 steps to the Siesta Key Public Beach

"Safe & Clean" Hide-A-Way Suite, only 60 steps to the Siesta Key Public Beach

1 bath
PoolA/CWiFiBalcony
$220/night
View Details → Book on VRBO
15 min walk to Siesta Key Village, Saltwater Pool/Spa, BBQ, Pond Views, Bike to Beach in 6 mins

15 min walk to Siesta Key Village, Saltwater Pool/Spa, BBQ, Pond Views, Bike to Beach in 6 mins

4 beds 2 baths
PoolA/CWiFiBalcony
$253/night
View Details → Book on VRBO
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

2 beds 2 baths
PoolA/CWiFiBalcony
$170/night
View Details → Book on VRBO
Beachside Vacation Cottage at Beach Palms

Beachside Vacation Cottage at Beach Palms

2 beds 1 bath
PoolA/CWiFiBalcony
$259/night
View Details → Book on VRBO
Updated in Tower, Private Beach, Heated Pool, WiFi

Updated in Tower, Private Beach, Heated Pool, WiFi

1 bed 1 bath
PoolA/CWiFiBalcony
$269/night
View Details → Book on VRBO
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US

WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US

2 beds 2 baths
PoolA/CWiFiBalcony
$267/night
View Details → Book on VRBO
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

2 beds 1 bath
PoolA/CWiFiBalcony
$229/night
View Details → Book on VRBO
LuLu Kemp Ridley, Walk to Beach, Heated Pool, BBQ

LuLu Kemp Ridley, Walk to Beach, Heated Pool, BBQ

1 bed 1 bath
PoolA/CWiFiBalcony
$180/night
View Details → Book on VRBO
Lower Pricing! Private Beach, 2 Heated Pools, Bay Sunrises

Lower Pricing! Private Beach, 2 Heated Pools, Bay Sunrises

2 beds 2 baths
PoolA/CWiFiBalcony
$217/night
View Details → Book on VRBO
Siesta Key, beach front condo on America's #1 Beach! 2 BR, 2 Bath, Sleeps 6

Siesta Key, beach front condo on America's #1 Beach! 2 BR, 2 Bath, Sleeps 6

2 beds 2 baths
PoolA/CWiFiBalcony
$326/night
View Details → Book on VRBO
Steps from Siesta Village and the Beach

Steps from Siesta Village and the Beach

1 bath
PoolA/CWiFiBalcony
$189/night
View Details → Book on VRBO
Prime Beachfront with Views, Views, Views!

Prime Beachfront with Views, Views, Views!

2 beds 2 baths
PoolA/CWiFiBalcony
$445/night
View Details → Book on VRBO
Siesta Key's PREMIER LOCATION with amazing beach view!

Siesta Key's PREMIER LOCATION with amazing beach view!

2 beds 1 bath
PoolA/CWiFiBalcony
$218/night
View Details → Book on VRBO
condo/on beach 1st floor/view of ocean from lanai siesta key beach

condo/on beach 1st floor/view of ocean from lanai siesta key beach

2 beds 2 baths
PoolA/CWiFiBalcony
$262/night
View Details → Book on VRBO
Location 1 Bdrm Cottage 1 Block from Beach and 2 Blocks from Siesta Village

Location 1 Bdrm Cottage 1 Block from Beach and 2 Blocks from Siesta Village

1 bed 1 bath
PoolA/CWiFiBalcony
$296/night
View Details → Book on VRBO
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.

2 beds 2 baths
PoolA/CWiFiBalcony
$352/night
View Details → Book on VRBO
Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$213/night
View Details → Book on VRBO
Amazing Beach Views, high floor-Steps to SK Beach. Romantic-Cozy-Quiet-Clean

Amazing Beach Views, high floor-Steps to SK Beach. Romantic-Cozy-Quiet-Clean

1 bed 1 bath
PoolA/CWiFiBalcony
$160/night
View Details → Book on VRBO
Top Rated Gulfside, White Sand Beach, 2 heated pools, pickleball/tennis, hot tub

Top Rated Gulfside, White Sand Beach, 2 heated pools, pickleball/tennis, hot tub

2 beds 2 baths
PoolA/CWiFiBalcony
$296/night
View Details → Book on VRBO
Our House at the Beach W-601 Luxury Quality Unit with Ocean View

Our House at the Beach W-601 Luxury Quality Unit with Ocean View

2 beds 2 baths
PoolA/CWiFiBalcony
$199/night
View Details → Book on VRBO
Fun-n-Sun Modern 2+2 Condo Steps to World famous Siesta Beach Pool Pickleball

Fun-n-Sun Modern 2+2 Condo Steps to World famous Siesta Beach Pool Pickleball

2 beds 2 baths
PoolA/CWiFiBalcony
$168/night
View Details → Book on VRBO
Palm Bay Club Siesta Key Newley renovated !

Palm Bay Club Siesta Key Newley renovated !

2 beds 2 baths
PoolA/CWiFiBalcony
$325/night
View Details → Book on VRBO
Siesta Key 3bdr Luxury - END UNIT RIGHT ON BEACH! - Gulf & Bay Club

Siesta Key 3bdr Luxury - END UNIT RIGHT ON BEACH! - Gulf & Bay Club

3 beds 3 baths
PoolA/CWiFiBalcony
$551/night
View Details → Book on VRBO
#1 SIESTA KEY Beach, Pool GlassHouse, CHECK our SPECIALS

#1 SIESTA KEY Beach, Pool GlassHouse, CHECK our SPECIALS

2 beds 2 baths
PoolA/CWiFiBalcony
$206/night
View Details → Book on VRBO
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

3 beds 2 baths
PoolA/CWiFiBalcony
$391/night
View Details → Book on VRBO

Showing 48 of 936 properties

More destinations in Florida

Panama City Beach (4614) Kissimmee (3730) Davenport (2507) Miami Beach (1899) Key West (1835) Cape Coral (1809) Sarasota (1719) Marco Island (1375) Naples (1355) Holmes Beach (770) Clearwater (768) Bradenton (551) Orlando (458) Miami (425) Anna Maria (386) Rotonda West (381) Clearwater Beach (361) Santa Rosa Beach (358) Destin (250) Gulf Shores (250)