Holiday Homes in Siesta Key

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Featured Holiday Homes in Siesta Key and around

Siesta Key Island Rentals
Room amenity
Siesta Key Island Rentals
3.0 star property
10.0 out of 10, Exceptional, (12)
"15 minute or less walk to everything you need. "
Siesta Key Island Rentals
Siesta Heron Suites & Villas
House, Lakeside | Private kitchen
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, (26)
"I like everything, thank you so much!!!"
The price is €390
per night
9 Jun - 10 Jun
Siesta Heron Suites & Villas
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Fridge, microwave, oven, stovetop
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
9.8 out of 10, Exceptional, (69)
"We booked this trip for our buddies wedding. The property was quiet and well maintained. We enjoyed our stay!"
The price is €626
per night
20 Jun - 21 Jun
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
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Retreat Half-Mile to Beach/Siesta Key Village
Fridge, microwave, stovetop, dishwasher
Retreat Half-Mile to Beach/Siesta Key Village
8.8 out of 10, Excellent, (25)
"Overall great experience. Home was close enough to the Siesta Village that we could walk. Close to market and trolley. Quiet neighborhood. House was clean and comfortable."
Retreat Half-Mile to Beach/Siesta Key Village
4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -
Beach nearby
4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -
10.0 out of 10, Exceptional, (165)
"This is our second trip to sea palm cottages in the last 8 months. The house is comfortable, the decor is lovely and the owners are delightful to work with. The pool is a backyard oasis and is an easy walk to white sand beaches and downtown restaurants and shops. We are already planning our next visit back!"
4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Beach nearby, sun-loungers, beach towels
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
9.6 out of 10, Exceptional, (100)
"This cottage is just steps away from the beach and Siesta Village with many restaurants, shops, and the market. You can park your car and never move it until check out. The cottage’s terrace was perfect for morning and nights. Everything was clean and neat. They have beach chairs (5 Tommy Bahama chairs), a cooler, beach cart, umbrella, and more. Keurig and drip coffee, everything we needed for the kitchen and plenty of paper supplies. We would definitely stay again."
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
On the beach, sun-loungers, beach umbrellas, beach towels
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
9.8 out of 10, Exceptional, (118)
"Excellent vacation property right at the beautiful Siesta beach. We've rented both units, so we had the whole house and pool area all to ourselves. All details in the house are well though through, house is extremely clean and quiet. Large bedroms wth comfortable beds and plenty of common space in the front unit, smaller space in the back unit. Variety of food delivery options from restaurants in the area. The beach is short stroll away, my 82 yrs old mom was easily making the walk without her...
The price is €2,803
per night
16 Jun - 17 Jun
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village
On the beach
Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village
9.8 out of 10, Exceptional, (17)
"The place was very nice. The bathroom situation was weird. It was a bit expensive and that stressed my mom out. The kitchen had everything you could possibly need. I wish I would have gotten a place with a pool. We loved the large living and dining area, the beds and pillows were not very comfortable"
Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village
Beautiful 3 bedroom/2.5 bath Condo On Siesta Key!
Exterior
Beautiful 3 bedroom/2.5 bath Condo On Siesta Key!
9.0 out of 10, Wonderful, (4)
"Perfect location across the street from the beach access. Management company slow to respond to issues with refrigerator and Wifi. Couldn't use freezer for most of the week and Wifi was never repaired the last 3 days of trip. Disappointing given the cost of this high-end rental where I would expect to be able to use the freezer to store groceries for the week. Instead we had to throw most of them out."
Beautiful 3 bedroom/2.5 bath Condo On Siesta Key!
Endless Views | Walking Distance To Siesta Key Beach + Village w/ Rooftop Panoramic Views!
Property grounds
Endless Views | Walking Distance To Siesta Key Beach + Village w/ Rooftop Panoramic Views!
10.0 out of 10, Exceptional, (21)
"This was the first Siesta Key visit for 4 out of 6 of us and we all had a terrific vacation. We spent a lot of time on the beach, used provided chairs and kayaks and took a charter boat one day (we highly recommend Key Life Charters). The Cottages management company was very responsive to a few issues we encountered (internet and elevator) during our stay. The kitchen was well stocked and the gas grill came in handy. The king beds were comfortable. We used Robinhood for bike rentals (they drop...
Endless Views | Walking Distance To Siesta Key Beach + Village w/ Rooftop Panoramic Views!
Beautiful HEATED pool home, bike to Siesta Key, quiet street, 1 MILE to beach
Terrace/patio
Beautiful HEATED pool home, bike to Siesta Key, quiet street, 1 MILE to beach
10.0 out of 10, Exceptional, (80)
"The house is beautiful and the heated, enclosed pool is perfect. Location is very close to market and beach entries. Very comfortable and the neighborhood is quiet and family friendly. I would recommend it for sure."
Beautiful HEATED pool home, bike to Siesta Key, quiet street, 1 MILE to beach
NEW: Steps to the BEACH! Lovely Beach House with a screened-in saltwater pool
Outdoor pool, a heated pool
NEW: Steps to the BEACH! Lovely Beach House with a screened-in saltwater pool
The price is €734
per night
4 Jun - 5 Jun
NEW: Steps to the BEACH! Lovely Beach House with a screened-in saltwater pool
Luxury Home w/ Heated Pool and Private Beach Access
Property grounds
Luxury Home w/ Heated Pool and Private Beach Access
9.4 out of 10, Exceptional, (88)
"Our family stayed here and found it to be a very clean and well kept property. The private beach access was great. The pool gets very little sun, but still nice."
Luxury Home w/ Heated Pool and Private Beach Access
Breathtaking Stunning Decor steps to private beach 3 night min any day of week
A heated pool
Breathtaking Stunning Decor steps to private beach 3 night min any day of week
9.8 out of 10, Exceptional, (65)
"We really enjoyed our stay in siesta key. The condo was clean and very well stocked with any extras a person might need like towels, dishwasher tablets, detergent, etc. it was also on the ground floor which was very convenient for unloading and loading the car. I was disappointed that we could not see the ocean from the condo. I thought I had filtered beachfront and oceanfront properties when we booked but maybe I didn’t. It was a very short walk to the beach. I was just hoping to soak in as...
The price is €779
per night
16 Jun - 17 Jun
Breathtaking Stunning Decor steps to private beach 3 night min any day of week
SKV 311 - Heated ❤ Pool, Walk to Village, Beach, Bars, Restaurants !!
Beach nearby
SKV 311 - Heated ❤ Pool, Walk to Village, Beach, Bars, Restaurants !!
9.4 out of 10, Exceptional, (22)
"Siesta Keys is a must visit 10 out of 10. Our accommodations were outstanding perfect location walking distance to everything a 10 out of 10."
SKV 311 - Heated ❤ Pool, Walk to Village, Beach, Bars, Restaurants !!
Beach Front and Walking Distance to Village
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Beach Front and Walking Distance to Village
9.0 out of 10, Wonderful, (22)
"We loved the top floor bedroom with open air view of the ocean. Kitchen worked great for us. Dining Table with view of the ocean made the food taste better. Stairs were a great workout but had to be careful. Garage was roomy but could use a caution strip where the floor bumper went up a few inches. We enjoyed using the grill. Trails walking to the ocean were fun and allowed us to avoid walking through tall grass."
Beach Front and Walking Distance to Village
Stunning 3 Bedroom/ 3 Bath Adjacent to Siesta Key Beach Access!
Property grounds
Stunning 3 Bedroom/ 3 Bath Adjacent to Siesta Key Beach Access!
7.0 out of 10, Good, (2)
"The property was nice, however it seemed a bit run down overall. The exterior of the building, the staircase, the windows were old and dirty. The jacuzzi tub was old and black chunks bubbled up when we tried to use it. The upstairs bathroom didn’t have a curtain and people down on the street could see my teenagers showering. The beds were very squeaky when you move. Very limited supply of towels/washcloths. I had to ask for more twice. Only four forks in the house, and had to ask for more from...
Stunning 3 Bedroom/ 3 Bath Adjacent to Siesta Key Beach Access!
:: Villa Oasis located in the heart of Siesta Key ::
Property grounds
:: Villa Oasis located in the heart of Siesta Key ::
10.0 out of 10, Exceptional, (21)
"Brigitte’s home was the perfect getaway, located in a quiet part of Siesta Key but still a short drive, walk or bike ride to town and beaches. The house was well stocked with plenty of beach gear, a grille, and other amenities. The house has a fabulous decor. We really enjoyed the pool area, which has different places to hang out. Brigitte was a wonderful host, available when needed or to answer questions. We hope to come back again."
:: Villa Oasis located in the heart of Siesta Key ::
Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!
TV
Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!
10.0 out of 10, Exceptional, (7)
"Hemingway House was perfect! The location was great .. close to the Siesta bridge. We were very comfortable and even used the pizza oven. It’s not so easy! Response to us was quick and immediate. I will say that supplies were limited… no start up food stuff in the kitchen. It was wonderful to get away!"
Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!
Admirals Watch | Ocean View w/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach
Fridge, microwave, oven, stovetop
Admirals Watch | Ocean View w/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach
9.6 out of 10, Exceptional, (31)
"Perfect location! Spacious 2 level unit with great views and comfortable furnishings. Pool was better than expected."
Admirals Watch | Ocean View w/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach
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See all available properties in Siesta Key
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.

Other property types in Siesta Key

Tropical Beach Resorts
Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4372)
"This resort was a great place to stay. Literally walking distance to a beautiful beach. Beach chairs and umbrellas available for purchase, beach towels provided free of charge. The kitchenette at this property was stocked with everything we needed. Room was clean and comfortable. Front office staff did a super quick check in. They have a movie dvd collection for in room entertainment. It would be awesome if the TVs were updated to have streaming apps such as Netflix. I would definitely return to...
The price is €163
per night
4 Jun - 5 Jun
Tropical Beach Resorts
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sports facility
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (164)
"The units are very spacious, clean and tastefully decorated. The pool is underwhelming as is the hot tub. Access to the beach was as advertised but losing the lounge chairs and umbrellas by 5:00 p.m.,hours before sunset is not ideal, especially for those with mobility issues who want to remain for the sunset, a highlight of the day. My children looked forward to paddle boarding and kayaking (as advertised) and inquired several times during our multiple day stay but were told none were available....
The price is €633
per night
19 Jun - 20 Jun
The Residences at Siesta Key Beach by Hyatt Vacation Club
The Ringling Beach House
Aerial view
The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (249)
"We’re a family of 4 and this was perfect for us! Very nice! We would definitely stay again! "
The Ringling Beach House
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.

Siesta Key Holiday Homes information

Number of reviews
829
Accommodation
644 Holiday Homes
Lowest Price
€390
Highest Price
€2,803

Recent Reviews in Siesta Key
Expedia verified reviews

The Ringling Beach House

The Ringling Beach House

5/5 Excellent
"We’re a family of 4 and this was perfect for us! Very nice! We would definitely stay again! "
A verified traveller stayed at The Ringling Beach House
Posted 1 day ago
The Ringling Beach House