Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 375 Rentals Available.
375 Vacation rentals
Filters applied: Waterfront
Casa Tegula – 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Child friendly
- Pet friendly
$380.00
from $380.00 / night
Casa Junonia - 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Child friendly
- Pet friendly
$345.00
from $345.00 / night
Casa Antilles – 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- 4 nights min
- Child friendly
- Pet friendly
$380.00
from $380.00 / night
Morgan Properties - Crescent Arms #703N - Updated 2 bed / 2 bath Gulf view
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$201.00
from $201.00 / night
Casa Eulimia – 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- 4 nights min
- Child friendly
$380.00
from $380.00 / night
Casa Stolida - 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Child friendly
- Pet friendly
$380.00
from $380.00 / night
Orchid Villa- 2BR, Sleeping Den, Heated Pool, 4 Min Walk to Beach [Sleeps 6]
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
- Pet friendly
$170.00
from $170.00 / night
Casita Morning Star – 3BR/3BA Private Heated Pool, Screened Lanai, Walk to Beach
Siesta Key House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
- Pet friendly
$240.00
from $240.00 / night
Casa Coquina – 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 14 14
- Min stay varies
- Child friendly
$380.00
from $380.00 / night
Morgan Properties - Sea Shell 406 - New Upgrades Throughout - Kitchen, Furniture
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$180.00
from $180.00 / night
$150.00
from $150.00 / night
The Pearl by the Sea -4/3 Waterfront, Heated Pool, w/Spa, Near Beach [Sleeps 10]
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
$256.00
from $256.00 / night
Peacock Villa – Gulfview, 3/3, Heated Pool, Near Village
Siesta Key Townhouse
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Child friendly
$240.00
from $240.00 / night
The Contento House
Siesta Key House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 1 mi
- Swimming pool
$201.00
from $201.00 / night
Casita Sun Star – 3BR/3BA Private Heated Pool, Screened Lanai, Walk to Beach
Siesta Key House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Child friendly
- Pet friendly
$240.00
from $240.00 / night
25% Discount April! - Siesta Dunes 2-108 - Renovated 2 Bed / 2 Bath Partial View
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$229.00
from $229.00 / night
Morgan Properties - Palm Bay Club #24-PARTIAL Gulf View-1 Bed/1Bath
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$140.00
from $140.00 / night
Villa Vista Mare
Siesta Key House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$326.00
from $326.00 / night
Casita Coco is a Completely Renovated 1/1 Heated Pool Home On Canal [sleeps 4]
Siesta Key House
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Child friendly
$101.00
from $101.00 / night
Morgan Properties - Sea Shell #208 - Newly Renovated 2 Bed / 2 Bath
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$180.00
from $180.00 / night
Tropical Beach Getaway at Sandy's Siesta!
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.01 mi
- Swimming pool
$125.00
from $125.00 / night
Villa Brisa Marina
Siesta Key House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$266.00
from $266.00 / night
Morgan Properties-Crystal Sands Villa 22-100% Renovated 2 Bed/2 Bath Close Beach
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$158.00
from $158.00 / night
The Big Kahuna – 8BR/6BA Private Home, Heated Pool, Private Cabana Walk to Beach
Siesta Key House
- 8 bedrooms 8
- 6 bathrooms
- Sleeps 24 24
- 4 nights min
- Child friendly
- Pet friendly
$712.00
from $712.00 / night
The Conch – 8BR/6BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 8 bedrooms 8
- 6 bathrooms
- Sleeps 12 12
- 4 nights min
- Child friendly
- Pet friendly
$712.00
from $712.00 / night
25% Discount April ! - Jamaica Royale #40 - Renovated 1 Bed / 1 Bath Condo
Siesta Key House
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$140.00
from $140.00 / night
Casita Playa- Playful 2BR, Private Beach Access, Communal Heated Pool [Sleeps 4]
Siesta Key House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 4 nights min
- Child friendly
- Pet friendly
$170.00
from $170.00 / night
25% Discount Apri - Brand NEW Siesta Dunes 2-205 2 Bed / 2 Bath Direct Oceanview
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$229.00
from $229.00 / night
Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 20% to 35% per Week*
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Nearest beach 0.1 mi
- Swimming pool
- Child friendly
$173.00
from $173.00 / night
Juicy Mango Cabana – 2/2, w/ Shared Heated Pool, Near Beach Access
Siesta Key Cottage
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 4 nights min
- Child friendly
$170.00
from $170.00 / night
CocoBayou Cottage 3/2 Heated Pool, Near Beach, Intercoastal, Village, Sleeps 10
Siesta Key House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
- Pet friendly
$240.00
from $240.00 / night
Casa De Mariposa – Gulf View, Heated Pool, 6/6 Near Village [sleeps 16]
Siesta Key House
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 16 16
- Min stay varies
- Child friendly
$415.00
from $415.00 / night
Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 20% to 35% per Week*
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Nearest beach 0.25 mi
- Swimming pool
- Child friendly
$101.00
from $101.00 / night
Charming Siesta Key Village Unbeatable Location
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- 3 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$150.00
from $150.00 / night
Morgan Properties - Crystal Sands Villa 6-Renovated 3 Bed/2 Bath Close to Beach!
Siesta Key Villa
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$215.00
from $215.00 / night
Morgan Properties - Sea Shell 102 - Updated 2 Bed / 2 Bath Direct Oceanview
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$180.00
from $180.00 / night
Villa De Paradisio
Siesta Key House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$235.00
from $235.00 / night
Morgan Properties - Crystal Sands 406 -BRAND NEW 1 Bed / 1 Bath Direct Ocean
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$215.00
from $215.00 / night
25% Discount April ! - Jamaica Royale #T54 - Ocean-front 2 Bed / 2 Bath Condo
Siesta Key House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$250.00
from $250.00 / night
Villa Trinidad – Hidden 4 BR Home on Canal, Heated Pool, w/Dock [Sleeps 10]
Siesta Key House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
- Pet friendly
$175.00
from $175.00 / night
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