Search Vacation Homes in Osprey

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Vacation Homes in Osprey

Beach towels
Charming Osprey Home

Vacation Home in Bay Acres

2.0 star property
The price is SAR 676
SAR 1,205 total
includes taxes & fees
8 Dec - 9 Dec
Charming Osprey Home
Fridge, microwave, oven, stovetop
#1 Vacation near Mineral Springs

Vacation Home in Warm Mineral Springs

10.0 out of 10, Exceptional, (8)
"Perfect spot for our weekend trip. "
United States
Andrea
The price is SAR 296
SAR 838 total
includes taxes & fees
6 Dec - 7 Dec
#1 Vacation near Mineral Springs
Beach
Charming 2-bedroom house in Englewood with WiFi and AC

Vacation Home in Englewood South

The price is SAR 450
SAR 1,125 total
includes taxes & fees
16 Dec - 17 Dec
Charming 2-bedroom house in Englewood with WiFi and AC
Dining
Nestled in North Port. Updated 2 Bed / 1 Bath.

Vacation Home in North Port

10.0 out of 10, Exceptional, (12)
"Very cute and cozy home in North Port FL close to shops and not a far drive to the beach. "
United States
James Y.
The price is SAR 251
SAR 736 total
includes taxes & fees
9 Dec - 10 Dec
Nestled in North Port. Updated 2 Bed / 1 Bath.
Beach nearby
Coastal duplex with private beach access & deck - dog-friendly

Vacation Home in Manasota Key

8.4 out of 10, Very Good, (12)
"Great place to stay. "
United States
Scott
The price is SAR 334
SAR 1,401 total
includes taxes & fees
7 Dec - 8 Dec
Coastal duplex with private beach access & deck - dog-friendly
Property grounds
Old Floridian cottage in Historic Gulf Village

Vacation Home in Olde Englewood Village

9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
The price is SAR 372
SAR 934 total
includes taxes & fees
6 Dec - 7 Dec
Old Floridian cottage in Historic Gulf Village
Fridge, microwave, oven, stovetop
New Two story Cozy House Near Warm Mineral Springs

Vacation Home in North Port

10.0 out of 10, Exceptional, (16)
"Had an awesome with friends and family and will stay again if we’re in the area."
United States
Eric H.
The price is SAR 422
SAR 1,714 total
includes taxes & fees
6 Dec - 7 Dec
New Two story Cozy House Near Warm Mineral Springs
Fridge, microwave, oven, stovetop
8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear

Vacation Home in South Venice

10.0 out of 10, Exceptional, (42)
"We had a wonderful time! The house was perfect and such a great location."
United States
Kellee N.
The price is SAR 355
SAR 1,264 total
includes taxes & fees
16 Dec - 17 Dec
8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Vacation Home in Siesta Key

3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is SAR 476
SAR 1,293 total
includes taxes & fees
18 Dec - 19 Dec
Siesta Heron Suites & Villas
Property grounds
Beautiful home with very private heated pool minutes from the beach

Vacation Home in South Venice

10.0 out of 10, Exceptional, (31)
"Great vacation home. Loved the pool area and great location. The home had everything you need for cooking or going to the beach. Manasota beach was great to spend the day. Thanks again for your beautiful vacation home!"
United States
mickey m.
Beautiful home with very private heated pool minutes from the beach
Dining
[escape to paradise] siesta key beach getaway

Vacation Home in Siesta Key

9.8 out of 10, Exceptional, (24)
"Clean and comfortable. "
United States
Laney
The price is SAR 305
SAR 1,056 total
includes taxes & fees
7 Dec - 8 Dec
[escape to paradise] siesta key beach getaway
Fridge, microwave, oven, stovetop
Myakka River

Vacation Home in Venice

9.8 out of 10, Exceptional, (18)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is SAR 694
SAR 1,709 total
includes taxes & fees
2 Jan - 3 January 2026
Myakka River
Outdoor dining
The Mermaid at Tiny House Siesta

Vacation Home in Sarasota

2.0 star property
10.0 out of 10, Exceptional, (2)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
The price is SAR 432
SAR 775 total
includes taxes & fees
8 Dec - 9 Dec
The Mermaid at Tiny House Siesta
Smart TV, Netflix, streaming services
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Vacation Home in Sarasota

9.4 out of 10, Exceptional, (17)
"Great location! Clean, easy to find and perfect amount of room. "
United States
Maribeliz G.
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Fridge, microwave, oven, stovetop
Retro-Inspired Stay, BBQ Patio, Close to Downtown

Vacation Home in Southgate

10.0 out of 10, Exceptional, (4)
"We loved the retro decor of the home, the comfy beds, and the great location! We loved being close to downtown Sarasota and to all the activities we attended! "
United States
Merita S.
The price is SAR 405
SAR 1,265 total
includes taxes & fees
8 Dec - 9 Dec
Retro-Inspired Stay, BBQ Patio, Close to Downtown
A heated pool
Relaxation Awaits: Luxurious Vacation Home with Heated Pool near Mineral Springs

Vacation Home in North Port

2.0 star property
10.0 out of 10, Exceptional, (6)
"This house is big and beautiful with all the amenities! Would definitely recommend to anyone!"
United States
Ashlee M.
Relaxation Awaits: Luxurious Vacation Home with Heated Pool near Mineral Springs
Fridge, microwave, oven, stovetop
Stylish house minutes from the beach

Vacation Home in South Venice

9.6 out of 10, Exceptional, (26)
"Great location and safe neighborhood. Definitely will stay again if available."
United States
Luis M.
Stylish house minutes from the beach
Property grounds
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Vacation Home in Sabal Harbour

2.0 star property
10.0 out of 10, Exceptional, (19)
"Everything was great!"
United States
Lisa and Colin M.
The price is SAR 456
SAR 1,290 total
includes taxes & fees
9 Dec - 10 Dec
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Fridge, microwave, oven, stovetop
Luxury Family Home Near Downtown & Siesta Key Beach

Vacation Home in Alta Vista

9.8 out of 10, Exceptional, (63)
"extremely comforting and accommodating for me and my friends. "
United States
Carolina V.
Luxury Family Home Near Downtown & Siesta Key Beach
Property grounds
Waterfront Getaway, a Boating Paradise

Vacation Home in Englewood

10.0 out of 10, Exceptional, (46)
"Great place to stay with your boat."
United States
arthur n.
The price is SAR 422
SAR 1,131 total
includes taxes & fees
6 Dec - 7 Dec
Waterfront Getaway, a Boating Paradise
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

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

10/10 Excellent
"Room was spotlessly clean and nicely upgraded. 5 min drive to Siesta Beach. Would definitely stay there again. Pool updated and beach towels and chairs provided for free for your trip to the beach. "
Alice 1-night trip
Posted 1 day ago
Hibiscus Suites - Gateway to Siesta Key