Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 333 Rentals Available.
333 Vacation rentals
Filters applied: Waterfront
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
Responds fast! Avg. 1 hour 33 minutes
$380.00
from $380.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$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
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 33 minutes
$380.00
from $380.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$310.00
from $310.00 / 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
Responds fast! Avg. 1 hour 37 minutes
$240.00
from $240.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$380.00
from $380.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$235.00
from $235.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$380.00
from $380.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 33 minutes
$255.00
from $255.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$170.00
from $170.00 / night
Siesta Key Beachfront Condo with Gulf View!
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$120.00
from $120.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$240.00
from $240.00 / 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
$85.00
from $85.00 / 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
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
Responds fast! Avg. 1 hour 33 minutes
$380.00
from $380.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$380.00
from $380.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$170.00
from $170.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$713.00
from $713.00 / night
Gorgeous Views of the Gulf Sea Turtle Unit Sunset Beach Resort
Siesta Key Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 2 nights min
- Child friendly
$510.00
from $510.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$713.00
from $713.00 / 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
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 33 minutes
$713.00
from $713.00 / night
Moonmist Waterside - 3BR on the Intracoastal Waterway Minutes from Siesta Beach
Siesta Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 33 minutes
$225.00
from $225.00 / night
Sophie’s Cottage- Waterfront 2/2 with Heated Pool Near Beach Access [Sleeps 8]
Siesta Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 33 minutes
$200.00
from $200.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$310.00
from $310.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$380.00
from $380.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$175.00
from $175.00 / night
2 BR, 2 Bath, Siesta Key Village Condo with Pool
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Nearest beach 0.1 mi
- Swimming pool
- Child friendly
$143.00
from $143.00 / night
Sea Shell Casita- Amazing 2BR Heated Pool Casita, Near Beach Access [Sleeps 6]
Siesta Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 33 minutes
$170.00
from $170.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$205.00
from $205.00 / 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
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
Responds fast! Avg. 1 hour 33 minutes
$170.00
from $170.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$270.00
from $270.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$235.00
from $235.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$170.00
from $170.00 / night
Honey Mango Cabana – 2/1, Shared Heated Pool, Near Beach Access
Siesta Key Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 33 minutes
$153.00
from $153.00 / 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
Responds fast! Avg. 1 hour 33 minutes
$170.00
from $170.00 / night
Siesta Key Beachfront 3 Bedroom Home, Sarasota
Siesta Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 9 9
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$395.00
from $395.00 / 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
$85.00
from $85.00 / night
Tropical Escape 1 Br Siesta Key Inn
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Ask about children
$199.00
from $199.00 / night
Gateway to Siesta Key 1/2 mile Walk Siesta Key Beach
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 56 minutes
$100.00
from $100.00 / night
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