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Compare 652 Vacation Homes in Siesta Key with updated reviews, rates, and availability.

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals

5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING

10.0 out of 10, Exceptional, (125)
"David was the property owner and easy to communicate with! We used both sides of this house- each side had its own kitchen and laundry! 6 bedrooms and plenty of outside deck space and a backyard pool. The beach chairs and umbrellas were a big help. We had everything we needed here for our Thanksgiving and wedding gathering. Thanks! The Arnold’s from Pittsburgh PA"
5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING

Toes In The Sand | Cottage with Private Pool, Walk to SK Beach and Village 🏝️ 🌅

2.0 star property
The price is SAR 3,531
SAR 6,734 total
includes taxes & fees
18 Jan - 19 January 2025
Toes In The Sand | Cottage with Private Pool, Walk to SK Beach and Village 🏝️ 🌅

Stunning Siesta Key,, . 50% OFF RATES, HEATED POOL, Book now HURRICANE SAFE

9.8 out of 10, Exceptional, (103)
"House is actually more beautiful than pictured! Everything you could need is at the house from pool toys, spices, shampoo/conditioner, soap, towels, etc. The house is beautiful and we had so much fun in the pool- definitely a trip to remember!!"
Stunning Siesta Key,, . 50% OFF RATES, HEATED POOL, Book now HURRICANE SAFE

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

9.6 out of 10, Exceptional, (88)
"Great, convenient location. Great communication. Very clean and great location."
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

[modern beach bungalow] garden views & patio

10.0 out of 10, Exceptional, (11)
"This property is nestled in a cute, quiet neighborhood and is within a 10 minute walk to the beach/restaurants/entertainment. The washer/dryer was a great amenity after a day at the beach!"
The price is SAR 352
SAR 1,340 total
includes taxes & fees
23 Dec - 24 Dec
[modern beach bungalow] garden views & patio

Tropical Oasis 5 min to Siesta Key, Private Salt Water Pool w Lanai!

10.0 out of 10, Exceptional, (54)
"Our week’s stay in Julia’s place was great. It was well stocked and she was a super communicator! The beds were very comfy and the pool, beautiful at night with the lighting and ambiance."
The price is SAR 1,315
SAR 2,829 total
includes taxes & fees
8 Jan - 9 January 2025
Tropical Oasis 5 min to Siesta Key, Private Salt Water Pool w Lanai!

No Hurricane Damage! 1 mile to Siesta! Low Wkly Rates! Pool & Spa! Fast Internet

9.6 out of 10, Exceptional, (114)
"Property was very clean and the owner, Ven, always made sure we had everything we needed. It was a great stay! Me and my family really liked it. We had a great time!"
No Hurricane Damage! 1 mile to Siesta! Low Wkly Rates! Pool & Spa! Fast Internet

Less than 5 minute walk to Siesta Key Beach.

2.0 star property
Less than 5 minute walk to Siesta Key Beach.

Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (113)
"We absolutely loved our bungalow and Lisa was the best. Unfortunately hurricane Helene blessed us with a visit. We made the decision to stay since the eye was in the panhandle. Bad decision. Lisa made sure we were safe and moved us to another property on higher ground and made arrangements for us to get off the island the day after. Above and beyond. Thank you for everything!"
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Steps to the ⭐ Beach, Short Walk to the Village

9.8 out of 10, Exceptional, (41)
"The property was situated perfectly where were wanted to be located. The mattress was extremely firm in all rooms. This might be for you but it wasn't for me. Some maintenance concerns were communicated to the property manager."
Steps to the ⭐ Beach, Short Walk to the Village

Beachside Retreat with Pool and Beach Access

9.2 out of 10, Wonderful, (32)
"See above "
Beachside Retreat with Pool and Beach Access

Clean Perfectly Remodeled Townhome, Steps From the Private Beach. 3 night min

9.8 out of 10, Exceptional, (194)
"It was clean and beautiful. We had a great time!!!"
Clean Perfectly Remodeled Townhome, Steps From the Private Beach. 3 night min

Perfect for Families, Steps to Siesta Key Beach and Village!

9.8 out of 10, Exceptional, (54)
"This property was perfect for a family stay as it was only 1 block away from the beach. It was so convenient. We enjoyed using the BBQ and being walking distance from the restaurants and shops as well. I highly recommend this property for a family vacation in Siesta Key."
Perfect for Families, Steps to Siesta Key Beach and Village!

Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

10.0 out of 10, Exceptional, (22)
"Like Goldie Locks says not to close and not to far .... JUST RIGHT everything you could possibly need, great restaurants, shopping, a small grocery that has every thing.. and the most Beautiful Beach you'll ever see. and I live in a beach town...."
The price is SAR 1,476
SAR 3,098 total
includes taxes & fees
5 Jan - 6 January 2025
Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Stunning Gulf Views! Walk to Siesta Key Beach, Private Pool/Spa & Waterfall

10.0 out of 10, Exceptional, (40)
"Great home. Well stocked with needed items, perfect location to village and beach."
Stunning Gulf Views! Walk to Siesta Key Beach, Private Pool/Spa & Waterfall

Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!

9.8 out of 10, Exceptional, (12)
"We really enjoyed our stay at the Hemingway home. The lay out was great and the kitchen was well equipped with cooking necessities. The location was great- however we came 3 weeks post hurricane Milton and the street that the house was/is on- was a destruction zone. There was so much debris on the sides of the road it looked like a war zone. The Hemingway way home was thankfully unscathed but I am pretty sure the surrounding houses were sadly very affected. The only real negative about the...
Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!

Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba

9.6 out of 10, Exceptional, (47)
"PERFECT FAMILY GETAWAY. As a busy family, we needed a decompression trip badly. This place was perfect; very clean interior, great backyard/ pool area and PERFECT location (though it’s not beach side, it’s just a block away from all the food and action in the Village, and short walk to access various beaches). The condo had plenty of room for a family of four (two very energetic and active teen boys), to live comfortably for a week without stepping all over one another. Could not have asked for...
Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba

Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

10.0 out of 10, Exceptional, (108)
"We had a fabulous week! Michelle was awesome! The condo was lovely & had everything we needed. It was located across the street from the Siesta Key Beach & close to the village. Would definitely recommend. "
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

Sun-Soaked & Relaxing Gem ~ Steps to Beach ~ Pool!

9.4 out of 10, Exceptional, (23)
"Short easy walk to the beach. For having just had a hurricane, the property was in great condition and everything was in working order. My only recommendation is if there are more than 4 guests, bring your own towels. Great location. Plenty of room. Had everything we needed."
Sun-Soaked & Relaxing Gem ~ Steps to Beach ~ 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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Other property types in Siesta Key

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
The price is SAR 674
SAR 846 total
includes taxes & fees
19 Jan - 20 January 2025
Tropical Beach Resorts

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (217)
"Awesome "
The price is SAR 1,809
SAR 2,235 total
includes taxes & fees
7 Jan - 8 January 2025
The Residences at Siesta Key Beach by Hyatt Vacation Club

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1057)
"Nice and quiet place, close to the beach and dining places."
The price is SAR 836
SAR 1,072 total
includes taxes & fees
29 Dec - 30 Dec
Captiva Beach Resort
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.