Search Vacation Homes in Siesta Key

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Vacation Homes in Siesta Key

Siesta Key Island Rentals
Enjoy cooking in this kitchen with a refrigerator, oven, and dishwasher, and a convenient green tiled backsplash.

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (42)
"Quiet neighborhood, clean and well maintained property, responsive management."
Siesta Key Island Rentals
Newly Renovated 2-bedroom w/Pool, Garage and a just a bike ride to Siesta Key!
Enjoy cooking in this kitchen with sleek cabinetry, a refrigerator, oven, and microwave.

Newly Renovated 2-bedroom w/Pool, Garage and a just a bike ride to Siesta Key!

9.4 out of 10, Exceptional, (23)
"Very good impression of the property. Can strongly recommend and very friendly communication with the host. "
Newly Renovated 2-bedroom w/Pool, Garage and a just a bike ride to Siesta Key!
Private Home Directly on Siesta Key Beach!
On the beach

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (2)
"The home was beautiful and well equipped and management was quick to respond to any questions that we had. Direct access to a gorgeous beach was definitely the highlight!! "
Private Home Directly on Siesta Key Beach!
Beachside Retreat with Pool and Beach Access
Enjoy a peaceful retreat on the balcony with a glass-top table and comfortable seating for four.

Beachside Retreat with Pool and Beach Access

8.8 out of 10, Excellent, (40)
"Great location for all our visitors to walk to many various restaurants and shops"
$1,004 nightly
The price is $1,119
Aug 7 - Aug 8
Total includes taxes and fees
Beachside Retreat with Pool and Beach Access
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Relax in this serene sunroom with a backyard view of the pool, featuring comfortable seating and a stone tile floor.

Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks

10.0 out of 10, Exceptional, (31)
"The house is a perfect place in a wonderfully located neighborhood. It is very clean and comfortable! Carrie is easy to communicate with. Just a fantastic place!"
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Guests can enjoy access to a wide, sandy beach with clear waters.

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (17)
"We had a great stay at this property! We had five adults and one infant with plenty of room to be comfortable. We enjoyed the short walk to the beach and that beach chairs were provided by the HOA (umbrellas are not but there was one at the property). The owners were wonderful, fast responses to any messages and made sure we had everything we needed to have a great time! Definitely recommend this property if you’re in Siesta Key and looking to be very close to the beach!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things
Enjoy a seamless flow between the kitchen and dining areas, featuring a large island with a sink and bar stools.

2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things

10.0 out of 10, Exceptional, (103)
"We had a great stay at this spacious, clean, conveniently located property"
2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things
Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!
Relax by the serene pool surrounded by lush greenery and palm trees.

Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!

9.6 out of 10, Exceptional, (77)
"Accommodations were perfect for our family Thanksgiving get away. "
$835 nightly
The price is $933
Sep 1 - Sep 2
Total includes taxes and fees
Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach
Enjoy stunning ocean views from this beachfront hotel's spacious rooms.

Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach

9.0 out of 10, Wonderful, (52)
"So close to the beach!"
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach
Sea Esta | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining
Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and a table for a leisurely escape.

Sea Esta | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

9.8 out of 10, Exceptional, (35)
"Amazing location to walk to beach and town. Place is really clean and well stocked with towels, kitchen needs and beach supplies. Would absolutely stay here again!"
Sea Esta | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining
Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!
Enjoy a serene beach experience with calm waters and ample space for relaxation and leisure activities.

Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!

10.0 out of 10, Exceptional, (15)
"The Home was incredible. It is completely updated and it was exceptionally clean. It is also in a great location. Also, the property managers were fantastic. Easy to reach and followed up during the stay to make sure everything was good. I highly recommend this home."
Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!
Luxury Home Steps from Siesta Key Beach with Game Room and Resort-Style Pool
Relax in a serene outdoor lounge with a hot tub, comfortable seating, and stunning views of the lush landscape and pool.

Luxury Home Steps from Siesta Key Beach with Game Room and Resort-Style Pool

8.4 out of 10, Very Good, (6)
"This place was incredible! Even better than we hoped for — super clean, beautifully decorated, and really well designed. The house had tons of space, great furniture, and everything was brand NEW! The pool, hot tub, and outdoor setup were amazing and made it hard to leave! Plus, it’s a very short walk to the beach, dining, entertainment, and even the trolley that takes you to the Village. You can tell a lot of thought went into every detail. We had an awesome stay and would definitely come back....
Luxury Home Steps from Siesta Key Beach with Game Room and Resort-Style Pool
Siesta Beach Cottage 3 Bedroom 2 Bath - Walk to Beach and Private Fishing Dock
Relax in a serene garden setting with a deck and comfortable seating for two.

Siesta Beach Cottage 3 Bedroom 2 Bath - Walk to Beach and Private Fishing Dock

10.0 out of 10, Exceptional, (16)
" Beautiful property with something for every age group! Quick to respond to any needs or questions and what seemed to be the Mayor of SK and maintenance was a pleasure to chat with. And make sure we had everything and more. "
Siesta Beach Cottage 3 Bedroom 2 Bath - Walk to Beach and Private Fishing Dock
Siesta Heron Suites & Villas
Enjoy cooking in this well-lit kitchen with a stainless steel range, sink, and coffee maker.

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very Good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
$297 nightly
The price is $336
Aug 10 - Aug 11
Total includes taxes and fees
Siesta Heron Suites & Villas
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Enjoy cooking in this kitchen with a central island, dishwasher, and stainless steel appliances.

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.6 out of 10, Exceptional, (100)
"We had a wonderful time and were very comfortable in this beautiful home. Loved the layout and the amenities. The pool was wonderful and warm. Siesta Key is our most favorite place to be. Thank you!"
$651 nightly
The price is $725
Aug 7 - Aug 8
Total includes taxes and fees
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Luxurious Paradise with Tiki Bar and Heated Pool, Just Remodeled!
Relax by the pool surrounded by lush greenery and palm trees.

Luxurious Paradise with Tiki Bar and Heated Pool, Just Remodeled!

9.8 out of 10, Exceptional, (7)
"The house was awesome, we love playing pool every night, we had awesome meals together, it's near every great restaurant and the square in Sarasota. Heidi recommended for anyone who wants to have an awesome family vacation."
Luxurious Paradise with Tiki Bar and Heated Pool, Just Remodeled!
Villa Vista Mare | Gorgeous Home w/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!
Guests can enjoy a day at the beach with umbrellas and a lifeguard tower nearby.

Villa Vista Mare | Gorgeous Home w/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!

10.0 out of 10, Exceptional, (52)
"We had a blast at this condo. Perfect location and accommodations!"
Villa Vista Mare | Gorgeous Home w/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3
Guests can enjoy a serene beach experience with access to the ocean.

Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3

9.8 out of 10, Exceptional, (98)
"So nice. Our unit had 2 comfortable king beds. So close to beach, with wagon, chairs and umbrella. Short walk to restaurants and shops, too! "
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Enjoy serene beach walks along the wide, sandy shoreline.

Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

9.6 out of 10, Exceptional, (109)
"Awesome location, perfect beach supplies provided, and VERY clean! "
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Steps From Siesta Key Beach! 1BR w/ Heated Pool
Enjoy the beachfront promenade and access to sandy beaches.

Steps From Siesta Key Beach! 1BR w/ Heated Pool

9.8 out of 10, Exceptional, (26)
"The place was perfect for us. It was great to have access to the private beach. The pool was very nice as well."
Steps From Siesta Key Beach! 1BR w/ Heated Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siesta Key Hotel Reviews

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Awesome"
Hector 2-night trip
Posted 2 hours ago
Siesta Key Beach Resort and Suites