Siesta Key Beach Rentals & Vacation Rentals - 187 Rentals Available
187 Vacation rentals
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
$200.00
from $200.00 / 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
$227.00
from $227.00 / 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
$226.00
from $226.00 / 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
$124.00
from $124.00 / 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
About Siesta Key
Things to do
If staying on dry land sounds like a bore, you'll find almost 50 miles of waterways and canals inside the island, not to mention the surrounding Gulf of Mexico and Sarasota and Roberts Bays. Many Siesta Key, FL vacation rentals provide boat docks, and boat rentals are available for you to get out and explore the waters. Other water sports are popular here as well, including fishing, snorkeling, parasailing, and sailboarding. If you'd rather not captain your own ship, plenty of local charter companies offer guided tours. Many of the local restaurants also offer temporary docking, so that you can go to dinner straight from your afternoon on the water. What better way to work up an appetite for some fresh seafood than a day spent in the sand, sun, and surf? We couldn't call it an "island paradise" if it didn't offer warm breezes, cool water, swaying palm trees, and some of the world's finest beaches, including Turtle Beach and Palmer Point Beach. Relaxing on the pure quartz beaches with family and friends is certainly a favorite pastime here, and visitors enjoy the charming beach hideaways and ample bird-watching opportunities. You might also spot some friendly dolphins and manatees dotting the surrounding gulf and bay waters.Climate
As a top Florida vacation destination you can imagine that Siesta Key offers flawless weather all year round. With over 250 sunny days per year, and a July high of 91 degrees, you're pretty much guaranteed a vacation unspoiled by the elements no matter when you visit. Try booking your trip for the "shoulder season" away from peak times or school vacations to keep crowds at bay. Low humidity makes Siesta Key comfortable, as well as warm.Events
If you visit the island during the beginning of May, the beach literally comes alive with figures made of sand during the island's unique sand sculpture contest that draws in world-class artists. Of course, anyone can try their hand at a sandcastle or sand sculpture any time of year. Take part in the Siesta Key drum circle on the Siesta Key public beach EVERY Sunday night. Beginning about an hour before sundown, instruments ranging from drums, flutes, guitars, shakers and cowbells create the circle. Be part of the audience, or participate with music and dance. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants. The Siesta Fiesta is in mid-April and celebrates local artisans while fostering a feeling of camraderie around the town.Food
After a day out on the beach or screaming while parasailing you're likely to work up an appetite. A place like Senor Siesta. rated #1 on TripAdvisor for Siesta Key restaurants, could fit the bill. With delicious and affordable latin cuisine available such as the empanada appetizer, you will be happy you chose to eat there. If you're looking for a more European flavor, why not try out Bonjour French Cafe & Crepes? For dessert, you should grab a scoop or three at Ciao Gelato or Big Olaf Cremery. Lastly, for a more down home feel, eat at The Cottage Restaurant which has all types of classic American dishes made to perfection. You won't go hungry in Siesta Key, trust us.All of this and more can be found within walking distance or a leisurely drive of Siesta Key vacation rentals, so start planning your trip today!
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.