Holiday Homes in Siesta Key, FL

Search among 400 available holiday homes in Siesta Key from 50+ providers.

Check-in
Sun, 12 Jan
-
Check-out
Mon, 13 Jan
Rooms and Guests2 Guests, 1 Room
Check-in
Sun, 12 Jan
-
Check-out
Mon, 13 Jan
Rooms and Guests2 Guests, 1 Room
1Filter & Sort
View map
Check-in
Sun, 12 Jan
-
Check-out
Mon, 13 Jan
Rooms and Guests2 Guests, 1 Room
1Filter & Sort
View map
View map
1-20 out of 400
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8.4
Great5 reviews
7 adults
3 bedrooms
4 beds
Map
4.7 km from City Centre
Offering an outdoor swimming pool with views of lake, the Siesta Heron Suites & Villas is located in the Siesta Key district of Siesta Key.
FromC$ 257 /nightSelect
6 adults
3 bedrooms
4 beds
Map
900 m from City Centre1.6 km from Siesta Beach
Situated in the Siesta Key district, the Siesta Key/ Derby Bay Villa Siesta Key overlooks the sea and features an outdoor pool.
FromC$ 340 /nightSelect
Map
1.9 km from City Centre200 m from Siesta Key Village
The Canal 313 - Right In Siesta Key Village! with a private pool is at a 3.9 km distance from Lido Key Beach.
FromC$ 945 /nightSelect
7 adults
Map
1.2 km from City Centre600 m from Siesta Beach
While staying at the Classic Siesta Key Beachfront Home you are invited to discover Siesta Key Village, set approximately a 15-minute walk away, or Siesta Key Beach, which is only 0.9 km away.
Select
4 adults
1 bedroom
2 beds
Map
700 m from City Centre1.4 km from Siesta Beach
While staying at the Sea Club II By Beachside Management Villa you are invited to discover Siesta Key Beach Access 2, set a 10-minute drive away, or Siesta Key Beach, which is a mere 1.3 km away.
FromC$ 246 /nightSelect
6 adults
2 bedrooms
3 beds
Map
2.3 km from City Centre
Staying at the smoke-free Sun And Sea By Beachside Management Villa Siesta Key, you can visit Edson Keith Estate, set nearly 5 minutes away by car, or simply relax by a swimming pool.
FromC$ 306 /nightSelect
8.0
Great2 reviews
5 adults
2 bedrooms
3 beds
Map
1.6 km from City Centre
Situated 650 metres from Crescent Beach, the Crescent Arms Condominiums also offers an outdoor pool.
FromC$ 804 /nightSelect
6 adults
2 bedrooms
3 beds
Map
4.3 km from City Centre
Offering a fully equipped kitchen complete with a microwave, a stove and a toaster, this villa is located close to Only France Cookies.
FromC$ 323 /nightSelect
6 adults
2 bedrooms
3 beds
Map
1.7 km from City Centre500 m from Siesta Key Village
Edson Keith Estate and Siesta Key Village are located 2.8 km and 1.2 km from the Cottage By The Sea By Beachside Management respectively.
FromC$ 192 /nightSelect
8 adults
Map
700 m from City Centre1.3 km from Siesta Beach
Situated in Siesta Key district, 20 km from Longboat Key, the venue boasts a sun terrace and a garden.
Select
9.0
Perfect1 review
2 adults
1 bedroom
2 beds
Map
1.3 km from City Centre700 m from Siesta Beach
Lido Key Beach is at a 4.9 km distance from the Island Rentals Siesta Key and Saint Armands Circle is 15 minutes' drive away.
FromC$ 984 /nightSelect
8.6
Great14 reviews
6 adults
2 bedrooms
3 beds
Map
700 m from City Centre1.4 km from Siesta Beach
Featuring a swimming pool, the Sea Club II By Beachside Management Siesta Key lies within 6 minutes' walk of Jamaica Royale.
FromC$ 361 /nightSelect
6.6
Nice2 reviews
6 adults
2 bedrooms
2 beds
Map
500 m from City Centre900 m from Siesta Beach
While staying at the Beach 5830 #T34 Villa Siesta Key you are invited to discover Edson Keith Estate, set a 5-minute ride away, or Big Sarasota Pass, which is a 10-minute drive away.
FromC$ 259 /nightSelect
5.6
Guest rating1 review
6 adults
2 bedrooms
3 beds
Map
2.7 km from City Centre
Nestled in the Siesta Key district, the Crescent Street Villas By Beachside Management is just 1.1 km from Siesta Key Marina.
FromC$ 363 /nightSelect
Map
2.6 km from City Centre
Select
Map
1.2 km from City Centre500 m from Siesta Beach
FromC$ 1 046 /nightSelect
Map
1000 m from City Centre300 m from Siesta Beach
FromC$ 758 /nightSelect
Map
1.3 km from City Centre700 m from Siesta Beach
FromC$ 1 099 /nightSelect
Map
1.2 km from City Centre500 m from Siesta Beach
FromC$ 1 522 /nightSelect
Map
2.7 km from City Centre
FromC$ 760 /nightSelect

FAQs about holiday houses in Siesta Key

If you want to book a holiday home in Siesta Key, these 9 recommendations may come in handy.

What are the most favoured pet-friendly holiday houses in Siesta Key?

According to iBooked.ca travel data, there are 3 accommodations that welcome pets. Check Wild Lime Cottage, offering an outdoor swimming pool, a heated pool and an outdoor pool on site. Another top villa is Beachpoint Cottages (rating: 8.0/10) with cots, snorkelling and diving.

Which Siesta Key holiday houses are family-friendly?

For a perfect family stay, check one of available deals on iBooked.ca. You may book Family Tides By Beachside Management for about 851C$ per night. This apartment is situated 3.4 km from Siesta Key Marina with an outdoor swimming pool, board games and a free car park on site.

What are the top holiday houses in Siesta Key offering hot tubs?

If you want to relax and unwind after a long day, there are 32 deals with hot tubs on iBooked.ca. Among them, we recommend Ocean Blue By Beachside Management rated 8.4/10 with an outdoor swimming pool, windsurfing and snorkelling on site. It costs 1243C$ per night. Alternatively, you may book Dockside Delight By Beachside Management with rating 8.0/10 for about 603C$ per night. It has an outdoor swimming pool, snorkelling and diving.

What are the top lakefront holiday houses in Siesta Key?

One of the top accommodations is Beachpoint Cottages at the cost of 336C$ with cots, snorkelling and diving.

What are the best holiday houses in Siesta Key which are good for couples?

According to iBooked.ca travel data, there are 24 deals for couples. Check Beachpoint Cottages (rating: 8.0/10), a top villa offering cots, snorkelling and diving, as well as concierge service, ironing and bicycle usage. It's set 20 minutes' walk from Siesta Beach Pavillion. Another great villa is A Shore Thing By Beachside Management at the price of 339C$ per night. Other suitable options for couples are Deja Blue One Of The Cottages On The Key, Sea Club II By Beachside Management and The Hummingbird By Beachside Management.

What are the best holiday houses in Siesta Key featuring a kitchen?

To stay at the top holiday house with a kitchen, iBooked.ca offers 11 properties to select from. If you enjoy cooking, book Island House Beach Resort with a rating 7.6/10 for 444C$ per night, providing an outdoor swimming pool, a business centre and a gaming room. Also we recommend Siesta Palms By The Beach with an outdoor swimming pool, a Jacuzzi and fishing on site. It offers rooms with a balcony, a sofa and a sitting area at the price of 410C$ per night.

What are the cheapest holiday houses in Siesta Key featuring free parking?

According to iBooked.ca travel data, there are 21 apartments to select from. For instance, you may book Buttonwood Cottage offering an outdoor swimming pool, free shuttle service and a heated swimming pool for 434C$ per night. Also you may book Crescent Arms Condominiums, a top villa with an outdoor swimming pool, windsurfing and canoeing. It costs 468C$ per night.

What are the top holiday houses in Siesta Key near Jamaica Royale?

If you want to stay near this tourist destination, iBooked.ca offers you 14 properties to select from. We recommend Sea Club II By Beachside Management rated 8.4/10, a top villa set a 10-minute walk from the landmark. It offers an outdoor swimming pool, snorkelling and canoeing. Another good option is Gorgeous Renovated Moonmist With Courtyard at the cost of 250C$ per night. Other top deals are Siesta Key/ Derby Bay and Bay Oaks - 6157 #E01.

What are the top luxury holiday houses in Siesta Key?

According to iBooked.ca travel data, one of the top holiday houses is Casa Siesta By Beachside Management, situated 350 metres from Siesta Key Drum Circle. It costs 290C$ per night.

Holiday Homes in Siesta Key essential information

🏨 Holiday Homes in Siesta Key 400
👛 Lowest price 192 CAD
✍️ Holiday Homes Reviews 25