Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 187 Rentals Available.
187 Vacation rentals
Filters applied: Waterfront
Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% 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
$124.00
from $124.00 / 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
Responds fast! Avg. 2 hours 37 minutes
$159.00
from $159.00 / night
Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% 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
$189.00
from $189.00 / night
Midnight Cove #714 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% 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
$124.00
from $124.00 / night
Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa
Siesta Key House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 13 13
- 7 nights min
- Swimming pool
- Child friendly
- Car not necessary
$659.00
from $659.00 / 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
$682.00
from $682.00 / night
Beautiful Condominium In Great Location !
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 14 nights min
- Swimming pool
- Child friendly
- Air conditioning
$89.00
from $89.00 / 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
$243.00
from $243.00 / night
Siesta Palms by the Beach - Sea Spray #123
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Gateway to Siesta Key 1/2 mile Walk Siesta Key Beach
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$138.00
from $138.00 / night
Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach
Siesta Key House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- 7 nights min
- Nearest beach 0.2 mi
- Swimming pool
- Child friendly
$880.00
from $880.00 / night
Charming Siesta Key Village Unbeatable Location
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$147.00
from $147.00 / 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
$101.00
from $101.00 / night
Siesta Key Inn - 1Br/1B Sabal Palm #2A
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$263.00
from $263.00 / 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
$199.00
from $199.00 / night
FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$236.00
from $236.00 / night
Large 1br/1ba vacation rental condo (780 Sq.Ft.)
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 1 night min
- Swimming pool
- Ask about children
- Air conditioning
$104.00
from $104.00 / night
Siesta Key Inn - 2Br/2B Royal Palm #2B
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Nearest beach 0.09 mi
- Swimming pool
- Ask about children
$304.00
from $304.00 / night
Three bedroom house directly on beach with gulf vi
Siesta Key House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 7 7
- min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$373.00
from $373.00 / night
Siesta Palms by the Beach - Sea Gem #124
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Siesta Key Inn 1Br/1B Pineapple Palm #2D
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Siesta Palms by Beach-3Br/2B Sea Dream #223
Siesta Key Condo
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$338.00
from $338.00 / night
Siesta Key Inn 1Br/1B Sabal Palm #1A
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$263.00
from $263.00 / night
Siesta Key Inn 2Br/2B Royal Palm #1B
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$304.00
from $304.00 / night
Siesta Key Inn 2Br/1B Majesty Palm #2C
Siesta Key Condo
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$287.00
from $287.00 / night
Siesta Key Inn 1Br/1B Pineapple Palm #1D
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Siesta Palms by the Beach - Sea Escape #225
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$304.00
from $304.00 / night
Siesta Key Inn 1Br1B Coconut Palm #1C
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Siesta Palms by the Beach - Sea Breeze #125
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Siesta Palms by the Beach - Sea Gem #224
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Siesta Palms by the Beach - Sea Breeze #126
Siesta Key Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Lovely Siesta Key 3BR 2.5BA Condo, Island Paradise
Siesta Key Condo
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$352.00
from $352.00 / night
Siesta Palms by the Beach - Sea Escape #226
Siesta Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Nearest beach 0.09 mi
- Swimming pool
- Child friendly
$304.00
from $304.00 / night
Chinaberry 436 at Midnight Cove Siesta Key
Siesta Key Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$228.00
from $228.00 / night
Buttonwood 477 at Midnight Cove Siesta Key, FL.
Siesta Key Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$243.00
from $243.00 / night
Firethorn 610 at Midnight Cove Siesta Key, FL.
Siesta Key Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$129.00
from $129.00 / night
Buttonwood 462 at Midnight Cove Siesta Key, FL.
Siesta Key Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$243.00
from $243.00 / night
Firethorn 320 at Midnight Cove Siesta Key, FL.
Siesta Key Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$225.00
from $225.00 / night
Firethorn 632 at Midnight Cove Siesta Key
Siesta Key Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$125.00
from $125.00 / night
Chinaberry 943 at Midnight Cove Siesta Key
Siesta Key Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$156.00
from $156.00 / night
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