Holiday Homes in Siesta Key

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Featured Holiday Homes in Siesta Key and around

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
NO STORM DAMAGE! 5 STAR SIESTA KEY BEACH, 80 STEPS to BEACH, RESORT POOL, 6 BED
10.0 out of 10, Exceptional, (124)
"The property is excellent. Location is ideal for beach. It is an easy 10 min walk to the village and 100 feet from beach access stop. You don’t have to worry about parking at all. The house is loaded with everything you need for going to the beach. Owner David is outstanding. Very easy to reach and prompt responding to texts . Exceptional stay. Highly recommended "
NO STORM DAMAGE! 5 STAR SIESTA KEY BEACH, 80 STEPS to BEACH, RESORT POOL, 6 BED
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
9.8 out of 10, Exceptional, (76)
"Great overall experience however, the cable and WiFi consistently loses connection, there’s a lack of privacy due to not curtains on the pool doors. Minor frustrations but overall great place to stay. "
The price is €506
includes taxes & fees
3 Nov - 4 Nov
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach
9.8 out of 10, Exceptional, (32)
"I came down from Tampa for a few days and this was perfect. It's walking distance to pretty much anything you'll need; grocery store, breakfast spot, 1mi to the beach. The house is adorable. Things to note: low ceilings (watch your head if you're tall), minimal dishes (brings your own), the Internet is super spotty (bring a hotspot). The area is nice and I walked my dog around a lot. There's also a couple free ride services that work on tips if you get tired or caught in the rain. I will...
The price is €192
includes taxes & fees
4 Nov - 5 Nov
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach
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
Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!
9.4 out of 10, Exceptional, (32)
"We liked this place a lot!! Definitely will come back!!"
Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!
HEATED pool, bike to Siesta, quiet street, 1 MILE to beach INTACT after storm
10.0 out of 10, Exceptional, (91)
"We had booked another rental in Siesta Key but after the hurricane came thru the rental was cancelled. Luckily we were able to book this house and it was very nice! In the pool everyday! Thank you.. Very comfortable place!"
HEATED pool, bike to Siesta, quiet street, 1 MILE to beach INTACT after storm
Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶
10.0 out of 10, Exceptional, (3)
"The house was perfectly set up for the beach with a family. Beach was perfect and 2 minute walk. House was gorgeous"
Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶
Private Home in Siesta Key, Florida Gulf of Mexico, USA
10.0 out of 10, Exceptional, (33)
"Our host, Paul, was incredibly nice and extremely responsive throughout the booking process and our stay. The home was very clean and had everything we needed stocked. There is lots of room in the home to spread out. The home itself is located incredibly close to every major activity in Sarasota. Everyone in our party was very pleased with our stay, and we are looking forward to potentially stay again in the future!"
Private Home in Siesta Key, Florida Gulf of Mexico, USA
Clean Modern Townhouse, Steps From PRIVATE Beach, heated pool, shuffle board
9.8 out of 10, Exceptional, (198)
"I was traveling with family and this was a great place. Location was perfect and we used the frog hop for a free shuttle around town. The kitchen was fully equipped and the place was very clean. The owner was excellent with communication. I’d definitely book here again! "
Clean Modern Townhouse, Steps From PRIVATE Beach, heated pool, shuffle board
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, (28)
"This place was great I highly recommend it . The bed was hard and not comfortable and the couch was not very comfortable but the location and cleanliness of this place was great . We would definitely come back and stay . "
Siesta Heron Suites & Villas
Spacious, beautifully decorated Townhouse ~ Private Beach~ Shuffleboard ~ Pool
9.8 out of 10, Exceptional, (68)
"Townhouse is beautiful, just steps to the beach. Amazing host, great location! Minor inconvenience of lots of construction in front of buildings, kinda loud and lots of construction vehicles."
Spacious, beautifully decorated Townhouse ~ Private Beach~ Shuffleboard ~ Pool
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach
9.2 out of 10, Wonderful, (48)
"My favorite beach is Siesta Key. I decided to spend my birthday weekend there with my husband but wanted to be walking distance to the beach. This place was not only that, but so cute inside. It is also walking distance to the restaurants and shops too."
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach
Beautiful 3 bedroom/2.5 bath Condo On Siesta Key!
9.2 out of 10, Wonderful, (5)
"My husband and I took our two adult kids along with their two friends and had a great time. The location was perfect for getting to the beach and all of the shops and restaurants. The property has a great view of the beach from the balcony and the home was very comfortable. All beach equipment was available too, which was super helpful! We can’t wait to return for another stay!"
Beautiful 3 bedroom/2.5 bath Condo On Siesta Key!
Siesta Key Village Home < Half Mi to Beach!
10.0 out of 10, Exceptional, (21)
"Loved our stay here. The place was amazing! The location was perfect, right in the center of the village and walking distance to the beach. The home was decorated beautifully, comfy and had all the tools for the beach. We absolutely loved our stay here. One of our favorite trips. "
Siesta Key Village Home < Half Mi to Beach!
GORGEOUS 3 Bedroom/2 Bath Home NEAR SIESTA KEY!
9.2 out of 10, Wonderful, (5)
"Great place! Quiet neighborhood. Close to everything."
GORGEOUS 3 Bedroom/2 Bath Home NEAR SIESTA KEY!
Newly Remodeled! Pool home near Siesta Beach!
10.0 out of 10, Exceptional, (21)
"We were in Siesta Key, at this beautiful home through TS Debby. Troy and Christine were amazing. Absolutely unmatched generosity and hospitality. This home is beautiful and in perfect condition. Everything is fresh and new. The outdoor space is amazing for hanging out all day and the fenced yard is a huge plus when traveling with your fur baby. We enjoyed the home but the real gem here are the hosts. We have stayed in MANY homes in this area and have never been so impressed with personal...
Newly Remodeled! Pool home near Siesta Beach!
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen
10.0 out of 10, Exceptional, (106)
"Perfect size for our group of 4. Very close to the beach and the village. Very nice premises. Everything you can possibly need is available in this townhouse."
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
10.0 out of 10, Exceptional, (36)
"Very impressive home with all the emminties. Location was perfect. Walking distance to the village and just steps across the street to the beach. Cannot wait to come back!"
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
9.8 out of 10, Exceptional, (35)
"Beautiful place. Lots of space. Excellent views comfortable furniture. "
The price is €1,593
includes taxes & fees
3 Nov - 4 Nov
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
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. "
Tropical Beach Resorts
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."
Captiva Beach Resort
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (208)
"Everyone on the staff was wonderful, fun and friendly! The resort is beautiful and soooo accommodating! "
The price is €489
includes taxes & fees
20 Nov - 21 Nov
The Residences at Siesta Key Beach by Hyatt Vacation Club
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.