Holiday rentals in Siesta Key, FL

Search among 469 available holiday rentals in Siesta Key from 50+ providers

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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$ 245 /nightSelect
8.6
Great22 reviews
The largest option:
8 adults
3 bedrooms
4 beds
Map
2.7 km from City Centre
Offering a swimming pool with views of patio, the Bianco Sands By Beachside Management is located in the Siesta Key district of Siesta Key.
FromC$ 193 /nightSelect
8.6
Great19 reviews
The largest option:
6 adults
2 bedrooms
3 beds
Map
2.1 km from City Centre400 m from Siesta Key Village
Sarasota Square is at a 6 km distance from the Beachpoint Cottages, while Siesta Key Drum Circle is about a 20-minute stroll away.
FromC$ 494 /nightSelect
8.4
Great22 reviews
The largest option:
7 adults
3 bedrooms
3 beds
Offering views of the patio, the beachfront Palm Bay Club is placed 6 minutes' stroll from Jamaica Royale and boasts a swimming pool.
FromC$ 758 /nightSelect
8.6
Great21 reviews
4 adults
1 bedroom
2 beds
Map
2.4 km from City Centre400 m from Siesta Key Village
Bay Island is within 3.1 km of the Gulf Holiday By Beachside Management Siesta Key and Shell Beach is a 5-minute drive away.
FromC$ 234 /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$ 184 /nightSelect
8.6
Great17 reviews
4 adults
2 bedrooms
2 beds
Map
1.9 km from City Centre
The Midnight Cove #532, Bayside In Siesta Key, Fl with a heated swimming pool is at 600 metres of Siesta Key Marina.
FromC$ 374 /nightSelect
8.6
Great20 reviews
6 adults
3 bedrooms
3 beds
Map
2.3 km from City Centre
Rooms of the beachfront Beach Residences On Siesta Aka The Hyatt face the beach and there is also a swimming pool on the premises.
FromC$ 1 117 /nightSelect
Siesta Key CondoApartment
6.4
Nice1 review
6 adults
2 bedrooms
2 beds
Map
500 m from City Centre1000 m from Siesta Beach
Nestled in the Siesta Key district of the city, the venue is about 20 km from Sarasota Bradenton International airport.
FromC$ 377 /nightSelect
8.8
Great16 reviews
The largest option:
2 adults
1 bedroom
1 bed
Map
6.3 km from City Centre
Featuring a year-round outdoor pool, the Inn At Turtle Beach Siesta Key in the Siesta Key district boasts 10 rooms.
FromC$ 288 /nightSelect
6 adults
2 bedrooms
2 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$ 292 /nightSelect
9.0
Perfect1 review
3 adults
1 bedroom
1 bed
Map
1000 m from City Centre300 m from Siesta Beach
Sitting within 3.3 km of Siesta Key Marina, the Beach - Bari 665 #2 is located in the Siesta Key district.
FromC$ 195 /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$ 344 /nightSelect
7.0
Very good1 review
5 adults
2 bedrooms
3 beds
Map
1.3 km from City Centre1.9 km from Siesta Beach
Located merely 5 minutes on foot from Crescent Arms, the Stay Siesta Dunes, #300; By Beachside Management Siesta Key offers moments of relaxation featuring a hot tub and an outdoor swimming pool.
FromC$ 1 150 /nightSelect
6 adults
2 bedrooms
2 beds
Map
500 m from City Centre900 m from Siesta Beach
The Jamaica Royale 101, 2 Bedrooms, 3 Heated Pools, Wifi, Sleeps 6 Siesta Key is situated in the Siesta Key district of Siesta Key, 26 minutes' drive from Sarasota Bradenton International airport.
FromC$ 263 /nightSelect
Map
2.1 km from City Centre200 m from Siesta Key Village
The Southern Comfort Villa Siesta Key is set 4.4 km from Saint Armands Circle and approximately 10 minutes' drive from Public beach.
FromC$ 526 /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$ 902 /nightSelect
4 adults
1 bedroom
1 bed
Map
1000 m from City Centre300 m from Siesta Beach
The Beach - Tropea 665 #3 Villa Siesta Key is nestled in the Siesta Key district, Crescent Beach is 2.5 km away.
FromC$ 307 /nightSelect
Island House Beach ResortApartment
8.0
Great3 reviews
The largest option:
4 adults
2 bedrooms
2 beds
Map
1.1 km from City Centre1.8 km from Siesta Beach
Situated only a 10-minute stroll from Crescent Beach, the Island House Beach Resort Siesta Key offers 80 guest rooms.
FromC$ 483 /nightSelect
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FAQs about holiday lettings in Siesta Key

Discover 10 answers from our FAQ and find your perfect holiday rentals in Siesta Key.

What are the top holiday rentals in Siesta Key Village district?

If you want to stay in Siesta Key Village district, check Avenida De Cortez By Beachside Management, which is situated a 30-minute walk from Shell Beach.

What are the top pet-friendly holiday rentals in Siesta Key?

Fanta Sea On The Beach By Beachside Management is the best pet-friendly weekend home in Siesta Key, in which prices start from 802C$.

What are the best cheap holiday rentals to stay in Siesta Key?

One of the top holiday lettings would be Sarasota Condo With Deck - Half Mile To Turtle Beach! from 236C$/night and Wild Lime Cottage from 277C$/night.
See more cheap holiday homes here.

How much does a 2-bedroom holiday house cost for a week?

A 2-bedroom holiday home in Siesta Key costs about 1077C$. Check this popular option: Villa W/ Pool, Walk To Stunning Siesta Key!.

How much does a 3-bedroom holiday house cost for a week?

For a 3-bedroom holiday rental in Siesta Key you might spend about 1141C$. Check this popular option — Siesta Key Beach - Cape Aqua 5545.

What are the most popular holiday rentals in Siesta Key near a beach?

If you are searching for a beach villa, Fins Up is a great option to consider.

What are the best holiday rentals with swimming pools in Siesta Key?

To swim and relax around the pool without leaving your holiday rental, stay at Beach Villas At The Oasis By Beachside Management, Jamaica Royal Beachfront By Beachside Management, or Siesta Key Condo. Other popular holiday places with swimming pools you can check here.

What are the top family-friendly holiday rentals in Siesta Key?

If you are travelling with kids, stay at Family Tides By Beachside Management in Siesta Key district.

What are the best Siesta Key holiday rentals with free parking?

If you want to park your car on site, check Siesta Key Beach - Bari 665 #2, in which prices start from 150C$.

What are the top holiday rentals near Venice, FL (VNC-Venice Municipal) airport?

If you're looking for a holiday apartment near Venice, FL (VNC-Venice Municipal) airport, take a look at Updated Apartment Walking Distance To Venice Beach or Aurora Seabreeze Three Bedroom Home.

Holiday rentals in Siesta Key

Handpicked holiday rentals in Siesta Key

Couples would enjoy staying in a holiday apartment with home-like atmosphere and all the comforts during their city escape. Those wishing to stay close to Siesta Key Beach can make a choice from 30 apartments and 39 villas. Find accommodation which suits you the most and get it booked!

Exclusive luxury places to stay in Siesta Key

Looking for the best luxury accommmodation in Siesta Key? iBooked.ca is here to help make your dreams come true. You can choose from around 39 villas to rent in Siesta Key within a walking distance of Siesta Key Beach. So if you are looking for a luxury place that includes high-end amenities in Siesta Key, iBooked.ca has all your travel needs sorted!

High graded cheap holiday homes in Siesta Key

The low price does not always mean low quality. No end of lower-cost holiday rentals are waiting for the budget traveller in Siesta Key. Cheap vacations houses near Siesta Key Beach are available on iBooked.ca if you are not planning to spend a lot during your vacations in Siesta Key. Check the options!

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Holiday rentals in Siesta Key essential information

🏨 Holiday rentals in Siesta Key 469
👛 Lowest price 163 CAD
✍️ Holiday rentals Reviews 283