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

Holiday Homes in Osprey

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Osprey holiday homes

House, Lakeside | Living area

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is €304
includes taxes & fees
22 Jul - 23 Jul
Siesta Heron Suites & Villas
Outdoor pool, a heated pool

The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (14 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is €244
includes taxes & fees
27 Jul - 28 Jul
The Dolphin
Dining

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

Beachside Bliss: Family House-Siesta Key-3BR/2BA
Sarasota
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for my family of 3 close to everything and a very quick drive to the beach! Comfortable beds and very clean! 10/10"
United States
Amanda C.
The price is €326
includes taxes & fees
20 Aug - 21 Aug
Beachside Bliss: Family House-Siesta Key-3BR/2BA
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (73 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is €363
includes taxes & fees
2 Aug - 3 Aug
Siesta Key Island Rentals
Interior

Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.
Sarasota Springs
10.0 out of 10, Exceptional, (1 review)
"Great 1 bedroom/1 bath in a quiet neighborhood. Friendly host. Accommodations were very accurately described. There is a mini fridge which was a nice convenience to have."
United States
Larry H.
The price is €109
includes taxes & fees
19 Aug - 20 Aug
Cozy 1-bedroom private room in Sarasota.
Coffee/tea maker, fridge, microwave, oven

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, (81 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 €225
includes taxes & fees
23 Jul - 24 Jul
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Beach nearby

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 €413
includes taxes & fees
11 Aug - 12 Aug
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Beach nearby, sun-loungers, beach towels

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Ridge Wood Heights
10.0 out of 10, Exceptional, (20 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
The price is €301
includes taxes & fees
22 Jul - 23 Jul
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Beach

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"The inside was very clean, we were very impressed! Being only a few minutes away from the beach, the location was perfect for what we had in mind. Area was surrounded by places to go shop as well. Would definitely stay again!"
United States
Jaret
The price is €178
includes taxes & fees
26 Jul - 27 Jul
The Mermaid at Tiny House Siesta
Coffee/tea maker, fridge, microwave, oven

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks
Nokomis
9.4 out of 10, Exceptional, (12 reviews)
"I’ve rented this property in the past and loved it! Convenient location, full stocked home, and comfy beds! "
United States
Christiann H.
MCM Waterfront Getaway w/ Private Dock + 4 Kayaks
Beach

Cozy Beach House Just Minutes From Siesta Key

Cozy Beach House Just Minutes From Siesta Key
Sarasota
9.0 out of 10, Wonderful, (17 reviews)
"Loved it"
United States
MIRIAM
The price is €252
includes taxes & fees
27 Jul - 28 Jul
Cozy Beach House Just Minutes From Siesta Key
On the beach, sun-loungers, beach towels

Dream Home at Sarasota Gulf Estates Heated pool

Dream Home at Sarasota Gulf Estates Heated pool
Sarasota
9.8 out of 10, Exceptional, (35 reviews)
"A great space for families with lots to do! Very clean, the host is very responsive, everything is as described. So glad we chose to stay here! Would definitely stay here again. "
United States
Matt N.
The price is €431
includes taxes & fees
20 Aug - 21 Aug
Dream Home at Sarasota Gulf Estates Heated pool
Terrace/patio

2 Bedroom 2 Bath home near Siesta Key Beach

2 Bedroom 2 Bath home near Siesta Key Beach
Sarasota
8.6 out of 10, Excellent, (40 reviews)
"Great little place -perfect for a few days in siesta "
United States
Linda K.
The price is €273
includes taxes & fees
22 Jul - 23 Jul
2 Bedroom 2 Bath home near Siesta Key Beach
2 bedrooms, iron/ironing board, WiFi, bed sheets

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is €260
includes taxes & fees
22 Jul - 23 Jul
[escape to paradise] siesta key beach getaway
Dining

Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key

Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key
Sarasota Springs
10.0 out of 10, Exceptional, (10 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is €317
includes taxes & fees
22 Jul - 23 Jul
Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key
Coffee/tea maker, fridge, microwave, oven

3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport

3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport
Siesta Key
9.0 out of 10, Wonderful, (31 reviews)
"Perfect spot to stay near Siesta Key village, would definitely stay here again! "
United States
Dale R.
The price is €311
includes taxes & fees
20 Aug - 21 Aug
3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport
Beach nearby, sun-loungers, beach towels

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, (45 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 €388
includes taxes & fees
22 Jul - 23 Jul
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
Beach

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
Siesta Key Village
9.6 out of 10, Exceptional, (22 reviews)
"Great location to walk to siesta key village. "
United States
N A.
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
Property grounds

Walk to the Beach | Osprey Villa | Siesta Key

Walk to the Beach | Osprey Villa | Siesta Key
Siesta Key Village
9.8 out of 10, Exceptional, (19 reviews)
"Host was very helpful. The apt was very comfy"
United States
Barbara B.
The price is €352
includes taxes & fees
19 Aug - 20 Aug
Walk to the Beach | Osprey Villa | Siesta Key
Beach towels

Poolside Paradise Near Siesta Key Beach

Poolside Paradise Near Siesta Key Beach
Bee Ridge
8.8 out of 10, Excellent, (12 reviews)
"Great house and great pool. AC struggled and there’s a bit of an ant problem, but overall great house. "
United States
Jake L.
The price is €418
includes taxes & fees
19 Aug - 20 Aug
Poolside Paradise Near Siesta Key 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"My family and I really enjoyed our stay at tropical breeze resort. The staff was superior especially Kate at the front desk. The best part was how close the the beach it was. We are already planning our next visit there. Thanks again staff at tropical breeze resort"
Sherry 2-night trip
Posted 7 hours ago
Tropical Breeze Resort

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
492
Accommodation
3956 Holiday Homes
Lowest Price
€109
Highest Price
€431