Osprey Vacation Rentals & Ski-in/Ski-out Homes
House
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
5 Guests
900 ft²
Parking
Kitchen
Air Conditioner
Internet
US $154/Night
7 Nights - US $1,081
House
- Sarasota
- ·
- Osprey Village
- 0.33 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
850.35 ft²
Oceanfront- Parking
Ocean View
Balcony/Terrace
US $230/Night
7 Nights - US $1,610
House
8.0Excellent
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
944 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $227/Night
7 Nights - US $1,590
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $163/Night
7 Nights - US $1,138
Apartment
9.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
592.02 ft²
- Oceanfront
Breakfast- Parking
Pool
US $216/Night
7 Nights - US $1,512
House
- Sarasota
- ·
- Osprey Village
- 0.28 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $305/Night
7 Nights - US $2,135
House
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
Hot Tub- Parking
- Ocean View
US $202/Night
7 Nights - US $1,413
Condo
- Sarasota
- ·
- Osprey Village
- 0.26 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $211/Night
7 Nights - US $1,480
Condo
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
595 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $202/Night
7 Nights - US $1,411
Luxury Places to Stay in Osprey
Over 118+ Luxury Places to Stay in or Near Osprey
House
10.0Exceptional
(27 Reviews)
5 Bedrooms
5 Baths
8 Guests
5000 ft²
Private Pool- Oceanfront
- Parking
- Pool
US $3,588/Night
7 Nights - US $25,117
House
- Sarasota
- ·
- Sorrento Shores
- 0.21 mi to center
5 Bedrooms
4 Baths
10 Guests
2830.91 ft²
Pet Friendly
Child Friendly
Security/Safety
US $2,026/Night
7 Nights - US $14,179
House
9.6Exceptional
(39 Reviews)
3 Bedrooms
2 Baths
6 Guests
2460 ft²
- Hot Tub
- Parking
- Balcony/Terrace
View
US $771/Night
7 Nights - US $5,400
New
House
- Sarasota
- ·
- Sorrento Shores
- 0.21 mi to center
5 Bedrooms
2 Baths
12 Guests
2832 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $733/Night
7 Nights - US $5,132
Condo
- Sarasota
- ·
- Sorrento Shores
- 0.28 mi to center
8.6Fabulous
(17 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $663/Night
7 Nights - US $4,640
Cottage
- Sarasota
- ·
- Osprey Village
- 0.35 mi to center
9.8Exceptional
(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $408/Night
7 Nights - US $2,853
House
3 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $382/Night
7 Nights - US $2,671
House
- Sarasota
- ·
- Sorrento Shores
- 0.32 mi to center
4 Bedrooms
2 Baths
10 Guests
2397 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $370/Night
7 Nights - US $2,592
RV Rental
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $366/Night
7 Nights - US $2,563
Top-Rated Vacation Rentals with a Pool in Osprey
Over 67+ Top-Rated Vacation Rentals with a Pool in or Near Osprey
Condo
10.0Exceptional
(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Ocean View
- View
US $243/Night
7 Nights - US $1,699
Condo
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
1900 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $157/Night
7 Nights - US $1,096
Condo
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
530 ft²
- Oceanfront
- Parking
- Pool
Spa
US $141/Night
7 Nights - US $987
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1589 ft²
- Pool
- Ocean View
- View
- Kitchen
US $292/Night
7 Nights - US $2,041
Condo
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
623 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $204/Night
7 Nights - US $1,427
House
9.8Exceptional
(62 Reviews)
3 Bedrooms
2 Baths
5 Guests
1471 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $301/Night
7 Nights - US $2,104
House
9.8Exceptional
(20 Reviews)
3 Bedrooms
2 Baths
6 Guests
1950 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $274/Night
7 Nights - US $1,919
House
- Sarasota
- ·
- Sorrento Shores
- 0.05 mi to center
9.8Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $229/Night
7 Nights - US $1,601
Condo
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
595 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $204/Night
7 Nights - US $1,430
Pet-Friendly Vacation Rentals in Osprey
Over 39+ Pet-Friendly Vacation Rentals in or Near Osprey
House
- Sarasota
- ·
- Osprey Village
- 0.13 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $309/Night
7 Nights - US $2,162
Hotel
8.1Excellent
(552 Reviews)
11 Baths
2755.56 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
US $114/Night
7 Nights - US $795
House
6.8Good
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
944 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $234/Night
7 Nights - US $1,635
RV Rental
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $366/Night
7 Nights - US $2,563
RV Rental
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $366/Night
7 Nights - US $2,563
House
2 Bedrooms
2 Baths
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $292/Night
7 Nights - US $2,046
Condo
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $130/Night
7 Nights - US $913
House
- Sarasota
- ·
- Osprey Village
- 0.41 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $226/Night
7 Nights - US $1,585
House
9.6Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
Laundry
US $107/Night
7 Nights - US $747
Large Vacation Homes & Villas in Osprey
Over 10+ Large Vacation Homes & Villas in or Near Osprey
House
7.4Very Good
(3 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $229/Night
7 Nights - US $1,604
House
4 Bedrooms
2 Baths
12 Guests
2400 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $252/Night
7 Nights - US $1,764
House
4 Bedrooms
3 Baths
12 Guests
3300 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $251/Night
7 Nights - US $1,755
House
2 Bedrooms
2 Baths
12 Guests
1887 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $312/Night
7 Nights - US $2,185
Villa
3 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
- Laundry
US $190/Night
7 Nights - US $1,330
Villa
- Sarasota
- ·
- Sorrento Shores
- 0.04 mi to center
9.0Exceptional
(22 Reviews)
5 Bedrooms
2 Baths
12 Guests
2800 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $656/Night
7 Nights - US $4,594
House
9.0Exceptional
(15 Reviews)
4 Bedrooms
2 Baths
13 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $587/Night
7 Nights - US $4,106
House
- Sarasota
- ·
- Sorrento Shores
- 0.32 mi to center
4 Bedrooms
2 Baths
12 Guests
2397 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $424/Night
7 Nights - US $2,965
House
- Sarasota
- ·
- Sorrento Shores
- 0.32 mi to center
4 Bedrooms
2 Baths
12 Guests
2397 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $410/Night
7 Nights - US $2,868
Wheelchair Accessible Vacation Homes in Osprey
Over 10+ Wheelchair Accessible Vacation Homes in or Near Osprey
Condo
9.2Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
595 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $241/Night
7 Nights - US $1,684
Condo
9.2Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
595 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $239/Night
7 Nights - US $1,674
Condo
8.8Fabulous
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
595 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $242/Night
7 Nights - US $1,695
Condo
1 Bedroom
1 Bath
4 Guests
623 ft²
- Balcony/Terrace
- Kitchen
- Child Friendly
Wheelchair Accessible
US $297/Night
7 Nights - US $2,082
Condo
1 Bedroom
1 Bath
2 Guests
595 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $205/Night
7 Nights - US $1,434
Condo
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $341/Night
7 Nights - US $2,386
Apartment
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $140/Night
7 Nights - US $980
Condo
3 Bedrooms
2 Baths
8 Guests
2058 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $258/Night
7 Nights - US $1,808
Condo
3 Bedrooms
3 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $218/Night
7 Nights - US $1,529
Osprey Resorts and Airbnb Homes Under $200
Over 35+ Osprey Resorts and Airbnb Homes Under $200
Apartment
9.8Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $155/Night
7 Nights - US $1,087
Apartment
1 Bedroom
1 Bath
4 Guests
624.31 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $183/Night
7 Nights - US $1,278
House
- Sarasota
- ·
- Osprey Village
- 0.14 mi to center
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $178/Night
7 Nights - US $1,246
Apartment
1 Bedroom
1 Bath
4 Guests
624.31 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $176/Night
7 Nights - US $1,232
Condo
1 Bedroom
1 Bath
2 Guests
623 ft²
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
US $119/Night
7 Nights - US $836
Condo
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Spa
US $103/Night
7 Nights - US $724
Apartment
- Sarasota
- ·
- Osprey Village
- 0.53 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $150/Night
7 Nights - US $1,050
Condo
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
3 Guests
735 ft²
- Oceanfront
- Parking
- Pool
- Spa
US $133/Night
7 Nights - US $931
Apartment
- Sarasota
- ·
- Osprey Village
- 0.22 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
630 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $152/Night
7 Nights - US $1,067
Instantly Bookable Vacation Homes in Osprey
Over 28+ Instantly Bookable Vacation Homes in or Near Osprey
House
- Sarasota
- ·
- Osprey Village
- 0.20 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
7 Guests
800 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $285/Night
7 Nights - US $1,997
RV Rental
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $366/Night
7 Nights - US $2,563
House
- Sarasota
- ·
- Osprey Village
- 0.42 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1336 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $440/Night
7 Nights - US $3,080
House
9.4Exceptional
(73 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $100/Night
7 Nights - US $700
Condo
- Sarasota
- ·
- Osprey Village
- 0.17 mi to center
9.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $153/Night
7 Nights - US $1,069
House
8.6Fabulous
(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $561/Night
7 Nights - US $3,929
House
8.0Excellent
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
943 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,728
House
6.8Good
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
944 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $226/Night
7 Nights - US $1,582
House
5.0Average
(3 Reviews)
3 Bedrooms
4 Baths
8 Guests
3042 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $491/Night
7 Nights - US $3,437
Book a Last Minute Place to Stay in Osprey
About Osprey Vacation Rentals
Explore over 127 vacation rentals in Osprey with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Osprey for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Osprey. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Osprey tailored to your preferences. On average, these rentals offer 821.7 ft² of space, and are priced at an average of US $300 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Osprey at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Osprey
| Type | Count |
|---|---|
| Vacation Homes | 68 |
| Holiday Apartments | 14 |
| Unique Vacation Rentals | 4 |
| Villas | 2 |
| Unique Vacation Rentals | 1 |
| Cottages | 1 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Osprey
★ Pro Tip: Discover Your Ideal Vacation Rental in Osprey with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Osprey, FL
View the weather forecast for Osprey before booking your Osprey Vacation Rentals to confirm your best time to go.
December - February
High 79°F Low 51°F
March - May
High 91°F Low 53°F
June - August
High 92°F Low 72°F
September - November
High 90°F Low 57°F
Top Attractions Around Osprey, FL
Sunski offers a large selection of top attractions around Osprey . Research things to do on your vacation before you visit Osprey.
Other Places to Stay in Osprey, FL
Frequently Asked Questions About Osprey?
What are the top vacation rentals in Osprey?
When organizing your trip to Osprey, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Osprey. Peruse our collection of highly-rated properties and secure your reservation today.
- Rare private beachfront estate on the Gulf.
- 2-bedroom Spacious townhome in Osprey
- Sarasota Vacation paradise!
- Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
- Sunny Coastal Escape
- Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
- Private guest house with king bed & loft. Deck with hot tub and putting green
- Renovated Tranquil 3-Bdrm- w/yard, workspace, great kitchen in Osprey dogs ok
- 2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!
- Windsor Lodge Unit #10 studio
How many vacation rentals have private pools in Osprey?
Uncover 10 vacation rentals boasting private pools near Osprey. Explore top-rated RBO homes offering access to a swimming pool:
- WATERFRONT Luxury Home! Private Pool, Dock, Close to Beaches
- Sarasota Home With Pool
- 15 mins from Beautiful Siesta Key Beach, Waterfront Home w/Private Pool
- Tropical canal front home in Osprey
Which vacation homes or resorts in Osprey are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Osprey. Enjoy great views, locations and save money with SunSki Resorts.™
How many SunSkiResorts vacation rentals or resorts are available in Osprey?
Discover the ideal vacation rental in Osprey with SunSki Resorts™. We provide an extensive selection of over 127 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Osprey.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| Vamo Vacation Rentals in Sarasota, Florida | 49 |
| Palmer Ranch Vacation Rentals in Sarasota, Florida | 36 |
| Sorrento Shores Vacation Rentals in Sarasota, Florida | 593 |
| Bay Acres Vacation Rentals in Sarasota, Florida | 739 |
| Rivendell Vacation Rentals in Sarasota, Florida | 395 |
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