Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 351 Rentals Available.
351 Vacation rentals
Filters applied: Waterfront
Siesta Key Beachfront Condo with Gulf View!
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$144.00
from $144.00 / 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
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$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
- Swimming pool
- Child friendly
- Air conditioning
$380.00
from $380.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
$240.00
from $240.00 / night
Villa Cascada- 4BR, 2 Kitchens, Heated Pool, Near Beach Access [Sleeps 12]
Siesta Key House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$310.00
from $310.00 / night
Midnight Cove #714 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
Casita Playa- Playful 2BR, Private Beach Access, Communal Heated Pool [Sleeps 4]
Siesta Key House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$170.00
from $170.00 / 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
Casa Ohana – 4BR/3BA Private Home, Heated Pool and Cabana, in Siesta Key Village
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$380.00
from $380.00 / 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
$147.00
from $147.00 / night
Villa De Paradisio- 4BR Waterfront Home on Canal, Heated Pool, w/Boat [Sleeps12]
Siesta Key House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$235.00
from $235.00 / night
Sea Wave Casita- Peaceful 2 BR, Heated Pool, 4 Min Walk to Beach [Sleeps 6]
Siesta Key House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$170.00
from $170.00 / 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
Casa Antilles – 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
- Swimming pool
- Child friendly
- Air conditioning
$380.00
from $380.00 / night
Villa Vista Mare - Luxurious 3BD/3BA Beachfront, Heated Pool
Siesta Key House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$380.00
from $380.00 / night
The Abalone – 8BR/6BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 8 bedrooms 8
- 6 bathrooms
- Sleeps 24 24
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$713.00
from $713.00 / night
Orchid Villa- 2BR, Sleeping Den, Heated Pool, 4 Min Walk to Beach [Sleeps 6]
Siesta Key House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$170.00
from $170.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
$240.00
from $240.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
$380.00
from $380.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
$380.00
from $380.00 / night
Sandy Cabana- 3BR, Heated Pool, Near Beach Access [Sleeps 8]
Siesta Key House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$206.00
from $206.00 / night
Pura Vida Oasis - 5BR Waterfront, Heated Pool, Spa near Village/Beach, Sleeps 13
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 13 13
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$270.00
from $270.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
$175.00
from $175.00 / night
Seaside Cottage - 4/3 Heated Pool Home On Siesta Key Beach Access [Sleeps 10]
Siesta Key Cottage
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 11 11
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$310.00
from $310.00 / night
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
- Swimming pool
- Child friendly
- Air conditioning
$380.00
from $380.00 / 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
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$713.00
from $713.00 / night
The Nautilus - 8BR/6BA Private Home, Heated Pool, Private Cabana, Walk to Beach
Siesta Key House
- 4 bedrooms 4
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$713.00
from $713.00 / night
Buccaneer’s Hideaway – 4BR/2.5BA Heated Pool, Dock, Canal, MInutes to Siesta Key
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$175.00
from $175.00 / night
Casita Bayou – Completely Renovated 2/1 Heated Pool Home On Canal [Sleeps 6]
Siesta Key House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 6 6
- Min stay varies
- Child friendly
- Pet friendly
$170.00
from $170.00 / night
Juicy Mango Cabana – 2/2, w/ Shared Heated Pool, Near Beach Access
Siesta Key Cottage
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$170.00
from $170.00 / night
Latitude Adjustment- 4 BR on Canal, Heated Pool, Private Dock [Sleeps 10]
Siesta Key House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$310.00
from $310.00 / night
Casita Mar- Beautiful 2 BR, Heated Pool, w/Spa, Private Beach Access [Sleeps 4]
Siesta Key House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$170.00
from $170.00 / night
The Canopy Cottage – 4/3 Private Pool and Spa, Near Siesta’s North Village
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Child friendly
- Pet friendly
$235.00
from $235.00 / night
Floritas Key is an encaptivating 3 BR + 2 BA Private Home, Heated Pool w/Spa
Siesta Key House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$150.00
from $150.00 / night
Mango Manor - Vibrant 4/3, W/Heated Pool, Right By Beach Access #13 [Sleeps 12]
Siesta Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$310.00
from $310.00 / night
Casa Costero- Breathtaking 3 BR in Siesta Key Village, w/Gulf Views [Sleeps 9]
Siesta Key Townhouse
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 9 9
- Min stay varies
- Child friendly
$240.00
from $240.00 / night
Coral Reef Casita- 2 BR Casita, Heated Pool, 4 Min Walk to Beach [Sleeps 6]
Siesta Key House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$170.00
from $170.00 / night
Beautiful Crescent Beach on Siesta Key One of the
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$186.00
from $186.00 / night
Siesta Key Beach Vacation
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- 14 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$81.00
from $81.00 / night
Morgan Properties - 308-2 Calle Miramar -PENTHOUSE + ROOFTOP 4 Bed/3 1/2 Bath
Siesta Key Condo
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$500.00
from $500.00 / night
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