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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Osprey holiday homes

An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees visible in the foreground.

1. Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
The price is £284
includes taxes & fees
31 Aug - 1 Sept
Charming Osprey Home
A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

2. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is £228
includes taxes & fees
31 Aug - 1 Sept
Siesta Heron Suites & Villas
A dining table set with plates, glasses, and a decorative glass holder.

3. Beachside Bliss: Family House-Siesta Key-3BR/2BA

Beachside Bliss: Family House-Siesta Key-3BR/2BA
Sarasota
10.0 out of 10, Exceptional, (28 reviews)
"Great property! Very clean and spacious. Perfect for what we needed and close to Siesta Key and Gulf Gate restaurants and bars,"
United States
Lori B.
The price is £246
includes taxes & fees
31 Aug - 1 Sept
Beachside Bliss: Family House-Siesta Key-3BR/2BA
A wooden pathway leading to a beach with clear turquoise water and a wooden railing on one side.

4. Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (268 reviews)
"It was amazing and way beyond what I thought. Easy walk to beach(0.4 mikes) and shops. Private location with small pool. Just what you need."
United States
Christina
The price is £79
includes taxes & fees
31 Aug - 1 Sept
Tropical Villas of Venice Beach
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

5. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is £236
includes taxes & fees
31 Aug - 1 Sept
Siesta Key Island Rentals
A beach with tall grasses and a sunset.

6. Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Siesta Key
9.2 out of 10, Wonderful, (38 reviews)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is £312
includes taxes & fees
31 Aug - 1 Sept
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

7. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (17 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is £181
includes taxes & fees
31 Aug - 1 Sept
The Dolphin
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

8. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is £208
includes taxes & fees
7 Sept - 8 Sept
[lounge like locals] walk to siesta beach +bikes
A beach with two wooden lounge chairs and a white umbrella.

9. Dream Home at Sarasota Gulf Estates Heated pool

Dream Home at Sarasota Gulf Estates Heated pool
Sarasota
9.8 out of 10, Exceptional, (38 reviews)
"Very clean, nice communicative hosts, you can tell they love that place there are a lot of cute personal touches. I felt safe here and it was quiet."
United States
jennifer w.
The price is £360
includes taxes & fees
31 Aug - 1 Sept
Dream Home at Sarasota Gulf Estates Heated pool
A covered outdoor area with a pool, seating, and a view of the water.

10. Oceanfront home w/sunset views of Sarasota Bay

Oceanfront home w/sunset views of Sarasota Bay
Vamo
9.8 out of 10, Exceptional, (132 reviews)
"Excellent place to stay"
United States
Bob E.
The price is £569
includes taxes & fees
19 Sept - 20 Sept
Oceanfront home w/sunset views of Sarasota Bay
A beach with waves and a bird flying near the shore.

11. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."
United States
Kadina A.
The price is £154
includes taxes & fees
31 Aug - 1 Sept
The Mermaid at Tiny House Siesta
A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

12. 3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!

3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
Gulf Gate Estates
10.0 out of 10, Exceptional, (24 reviews)
"Family had a great vacation at this property in Gulf Gate. Very nice pool and deck area and comfortable and clean home, great location for Siesta and Turtle beaches. Host was responsive and a pleasure to deal with, check in/out very simple. We were happy with our stay. "
United States
Martin F.
The price is £463
includes taxes & fees
31 Aug - 1 Sept
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
A modern kitchen with white cabinets, a dining area with a dark wooden table set for four, and a chandelier.

13. Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
Sarasota Springs
10.0 out of 10, Exceptional, (13 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is £240
includes taxes & fees
31 Aug - 1 Sept
Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
A clear swimming pool with a pink float, surrounded by a covered area with chairs and a wooden fence.

14. Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Ridge Wood Heights
9.4 out of 10, Exceptional, (125 reviews)
"very convenient, it was right in front of the event center that my daughter was dancing."
United States
erica
The price is £208
includes taxes & fees
1 Sept - 2 Sept
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a tiled backsplash.

15. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (84 reviews)
"Her stay was outstanding everything was so professionally ready for us we felt at home comfortable the Privacy was impeccable"
United States
James W.
The price is £190
includes taxes & fees
7 Sept - 8 Sept
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

16. Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
Nokomis
10.0 out of 10, Exceptional, (18 reviews)
"Great place close to beach and great food restaurants "
United States
Adan M.
The price is £281
includes taxes & fees
31 Aug - 1 Sept
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

17. Sea Turtle- Full Sized living at Tiny House Siesta

Sea Turtle- Full Sized living at Tiny House Siesta
Sarasota
9.4 out of 10, Exceptional, (18 reviews)
"The Tiny House is a perfect location to explore Siesta Key and the surrounding areas. It had just what we needed but was in close proximity (walking distance) to many bars and restaurants but was still exceptionally quiet."
United States
Wayne
The price is £172
includes taxes & fees
31 Aug - 1 Sept
Sea Turtle- Full Sized living at Tiny House Siesta
A lifeguard tower with a red exterior, a flagpole with an American flag, and a beach with people and buildings in the background.

18. Poolside Paradise Near Siesta Key Beach

Poolside Paradise Near Siesta Key Beach
Bee Ridge
8.8 out of 10, Excellent, (12 reviews)
"Our family of 11 had a truly wonderful stay. The pool was most definitely a highlight."
United States
Fannie Marie S.
The price is £317
includes taxes & fees
2 Sept - 3 Sept
Poolside Paradise Near Siesta Key Beach
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

19. Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village
Siesta Key Village
8.4 out of 10, Very good, (14 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is £281
includes taxes & fees
1 Sept - 2 Sept
Island Villa | Cozy Beach Retreat | Walk to Village
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

20. Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
Nokomis
10.0 out of 10, Exceptional, (46 reviews)
"Great spot close to many attractions. Very well appointed with all that you need for a great vacation!"
United States
Suzanne G.
The price is £333
includes taxes & fees
1 Sept - 2 Sept
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
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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Top Osprey Hotel Reviews

Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"La atención de las personas en el hotel"
Erick 1-night trip
Posted 6 hours ago
Lido Beach Resort

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
884
Accommodation
3972 Holiday Homes
Lowest Price
£79
Highest Price
£569