A marina with docked boats, a wooden bridge, and a building with a red roof.

Search Holiday Homes in Osprey

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Osprey holiday homes

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.

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is £237
includes taxes & fees
15 Oct - 16 Oct
Siesta Heron Suites & Villas
A modern kitchen with a stainless steel sink, a dining area with a table and chairs, and a living room with a sofa and a TV.

2. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (93 reviews)
"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."
United States
Ashley H.
The price is £478
includes taxes & fees
28 Oct - 29 Oct
Oceanfront home
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)
"Very nice place to stay and very relaxing. Clean, organized, and has everything you could possibly need. Host was very nice, quick to respond, and thoughtful. Would recommend to anyone and will definitely be staying again in future."
United States
Jessica R.
The price is £261
includes taxes & fees
15 Oct - 16 Oct
Beachside Bliss: Family House-Siesta Key-3BR/2BA
A beach with tall grasses and a sunset.

4. 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)
"This is a beautiful place."
United States
Pam J.
The price is £337
includes taxes & fees
26 Oct - 27 Oct
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
A modern kitchen with stainless steel appliances, a dining area with a round table and chairs, and a large window overlooking a backyard.

5. KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Gulf Gate Estates
10.0 out of 10, Exceptional, (45 reviews)
"Our 2nd time here and we’ll be back again! Thanks Tim and family for such a great house!"
United States
Angela K.
The price is £420
includes taxes & fees
23 Oct - 24 Oct
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
A beach with waves and a bird flying near the shore.

6. 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 £135
includes taxes & fees
17 Oct - 18 Oct
The Mermaid at Tiny House Siesta
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

7. 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 £150
includes taxes & fees
26 Oct - 27 Oct
Sea Turtle- Full Sized living at Tiny House Siesta
A covered patio with a round table and chairs, large windows, and a view of a backyard with a wooden fence and palm trees.

8. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key
Sarasota
9.8 out of 10, Exceptional, (85 reviews)
"Clean and convenient"
United States
Scott H.
2 miles to #1 Beach Siesta Key
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

9. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is £257
includes taxes & fees
15 Oct - 16 Oct
The Dolphin
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

10. 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 £276
includes taxes & fees
15 Oct - 16 Oct
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

11. 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, (27 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 £512
includes taxes & fees
3 Nov - 4 Nov
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 stainless steel refrigerator, and a large island with bar stools.

12. [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)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is £229
includes taxes & fees
15 Oct - 16 Oct
[lounge like locals] walk to siesta beach +bikes
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

13. Dolphin Villa | Pool | Steps to Siesta Key Village

Dolphin Villa | Pool | Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is £283
includes taxes & fees
22 Oct - 23 Oct
Dolphin Villa | Pool | Steps to Siesta Key Village
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, (128 reviews)
"Barb was very helpful and made numerous quality suggestions for nearby restaurants and activities."
United States
Mitzy B.
The price is £214
includes taxes & fees
15 Oct - 16 Oct
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
A narrow hallway leading to a bathroom with a vanity, shelves with storage bins, and a chandelier.

15. Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.
Sarasota Springs
10.0 out of 10, Exceptional, (7 reviews)
The price is £95
includes taxes & fees
26 Oct - 27 Oct
Cozy 1-bedroom private room in Sarasota.
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

16. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (221 reviews)
"Nice stay perfect location"
United States
tom f.
The price is £363
includes taxes & fees
21 Oct - 22 Oct
Siesta beach....one and only
A lifeguard tower with a red exterior, a flagpole with an American flag, and a beach with people and buildings in the background.

17. Poolside Paradise Near Siesta Key Beach

Poolside Paradise Near Siesta Key Beach
Bee Ridge
8.8 out of 10, Excellent, (13 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 £336
includes taxes & fees
19 Oct - 20 Oct
Poolside Paradise Near Siesta Key Beach
A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

18. Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
South Village
9.6 out of 10, Exceptional, (72 reviews)
"It was very clean and close to the beach. Perfect location."
United States
Cortney
The price is £477
includes taxes & fees
15 Oct - 16 Oct
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
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 £299
includes taxes & fees
20 Oct - 21 Oct
Island Villa | Cozy Beach Retreat | Walk to Village
A coastal hotel with multiple buildings, a beach, and ocean waves.

20. Key Life Reef l Semi-Private Pool, Walk to the Beach!

Key Life Reef l Semi-Private Pool, Walk to the Beach!
Siesta Key
9.4 out of 10, Exceptional, (8 reviews)
"Exactly what we were looking for. A place near the beach with a pool. Clean, modern, attentive manager. Would recommend highly."
United States
isabel b.
The price is £576
includes taxes & fees
28 Oct - 29 Oct
Key Life Reef l Semi-Private Pool, Walk to the Beach!
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
"Beautiful beach view"
María 1-night trip
Posted 2 hours ago
Lido Beach Resort

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
692
Accommodation
3973 Holiday Homes
Lowest Price
£95
Highest Price
£576