Search Villas in Osprey

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Featured Villas in Osprey

Paradise Cove at Lemon Bay
Private beach, white sand, snorkelling, kayaking

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very good, (78)
"I loved the property and the host was also very professional. "
Paradise Cove at Lemon Bay
Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches
Dining

Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches

9.8 out of 10, Exceptional, (13)
"This is the third time we have stayed here and have a great time every time. It is a spacious home in the perfect location. Close to downtown but quiet and safe neighborhood. "
Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches
NEW 3BR Home with Pool, Hot Tub, Cafe, Minutes to Venice and Englewood Beaches
A heated pool

NEW 3BR Home with Pool, Hot Tub, Cafe, Minutes to Venice and Englewood Beaches

10.0 out of 10, Exceptional, (1)
"Beautiful house!"
NEW 3BR Home with Pool, Hot Tub, Cafe, Minutes to Venice and Englewood Beaches
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
A heated pool

"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath

10.0 out of 10, Exceptional, (16)
"Our favorite place we have stayed at manasota key ever"
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
Waterfront Mermaid's Retreat Delights!
A heated pool

Waterfront Mermaid's Retreat Delights!

9.8 out of 10, Exceptional, (67)
"The property was awesome. Great place to stay. Close to beach ."
Waterfront Mermaid's Retreat Delights!
Spacious Villa with Lush Tropical Garden Very Close to Siesta Key!
Exterior

Spacious Villa with Lush Tropical Garden Very Close to Siesta Key!

10.0 out of 10, Exceptional, (66)
"Great place near the beach ! "
Spacious Villa with Lush Tropical Garden Very Close to Siesta Key!
2 bed/2 Ba Venice Island Villa - Walk to Beach & Historic Downtown Venice!
Beach nearby

2 bed/2 Ba Venice Island Villa - Walk to Beach & Historic Downtown Venice!

9.8 out of 10, Exceptional, (16)
"Beautiful place, very accommodating, and owner was very kind, responsive, and knowledgeable. Would definitely stay again in the future!"
2 bed/2 Ba Venice Island Villa - Walk to Beach & Historic Downtown Venice!
Major Upgrades 1 of a kind home right on the beach
Property grounds

Major Upgrades 1 of a kind home right on the beach

10.0 out of 10, Exceptional, (118)
"Everything was in perfect order at this property! Loved our stay here!"
Major Upgrades 1 of a kind home right on the beach
Updated Downtown Sarasota Villa, 2b/2b
Exterior

Updated Downtown Sarasota Villa, 2b/2b

9.6 out of 10, Exceptional, (7)
"Would stay again "
Updated Downtown Sarasota Villa, 2b/2b
Salty Shell Villa 5 star rated minutes to Warm Mineral Springs and area beaches!
Outdoor pool

Salty Shell Villa 5 star rated minutes to Warm Mineral Springs and area beaches!

9.6 out of 10, Exceptional, (5)
"Excellent place"
Salty Shell Villa 5 star rated minutes to Warm Mineral Springs and area beaches!
Stunning Sunrise Deluxe-Heated Pool & Spa Villa-Awesome Amenities-Min to Beach
Outdoor pool, a heated pool, pool loungers

Stunning Sunrise Deluxe-Heated Pool & Spa Villa-Awesome Amenities-Min to Beach

10.0 out of 10, Exceptional, (54)
"I absolutely loved our stay at this home. The home was beautiful, the neighborhood quiet, and located close to restaurants, grocery stores, and beach. I 100% recommend this property to anyone searching, and I hope to visit again the next time we are in Florida. "
Stunning Sunrise Deluxe-Heated Pool & Spa Villa-Awesome Amenities-Min to Beach
Renovated 1 Bed / 1 Bath Condo on Siesta Beach!
Pool

Renovated 1 Bed / 1 Bath Condo on Siesta Beach!

10.0 out of 10, Exceptional, (6)
"Best place to stay"
Renovated 1 Bed / 1 Bath Condo on Siesta Beach!
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Property grounds

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

8.6 out of 10, Excellent, (4)
"Perfect house with everything you need, we enjoyed it! "
The price is NZ$1,675
includes taxes & fees
29 Sept - 30 Sept
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Luxury Villa steps from Venice Beach Children friendly
Exterior

Luxury Villa steps from Venice Beach Children friendly

9.4 out of 10, Exceptional, (110)
"Very close to beach grandkids loved the loft beds"
Luxury Villa steps from Venice Beach Children friendly
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Exterior

Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

10.0 out of 10, Exceptional, (7)
"Host was great with all communication , place is stunning and the area is perfect "
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Outdoor dining

Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!

10.0 out of 10, Exceptional, (18)
"The house was nice and had almost anything you might need for a short stay."
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Luxury Tropical Retreat, Pool, King Beds & Game Room
Outdoor dining

Luxury Tropical Retreat, Pool, King Beds & Game Room

2.0 star property
10.0 out of 10, Exceptional, (10)
"We loved our staycation at this clean, well-equipped home! Lots of thoughtful details went into planning, decorating & outfitting. We were very comfortable & able to stretch out in all the various spaces inside & outside! 5 Stars all around!!!"
Luxury Tropical Retreat, Pool, King Beds & Game Room
Peaceful Beach Home Fully Equipped!
Exterior

Peaceful Beach Home Fully Equipped!

9.4 out of 10, Exceptional, (3)
"We had never been to Sarasota before and were thrilled with the location of this Vacation Rental. Walking/biking (Legacy Trail) distance to parks, groceries, and museums on a quiet dead end street. Easy access to beaches, theaters, and friends on various Keys. The home itself was super clean and comfortable supplied with everything we might need. The owner was exceptionally respectful of our privacy and immediately responsive for any questions we had. We would definitely stay there again."
Peaceful Beach Home Fully Equipped!
Walk to Beach & Historic Downtown Venice - Rennovated 2 Bed, 2.5 Ba, off-st pkg
Property grounds

Walk to Beach & Historic Downtown Venice - Rennovated 2 Bed, 2.5 Ba, off-st pkg

10.0 out of 10, Exceptional, (11)
"Wonderful place in a great neighborhood. Had everything we needed. Would stay here again."
Walk to Beach & Historic Downtown Venice - Rennovated 2 Bed, 2.5 Ba, off-st pkg
Sparkling Clean Villa at Vista Hermosa. Walk to Beach, Dining, Shopping & More 167
Beach nearby, sun-loungers, beach towels

Sparkling Clean Villa at Vista Hermosa. Walk to Beach, Dining, Shopping & More 167

10.0 out of 10, Exceptional, (4)
"Great residence, recently renovated, comfortable beds, nice layout, quiet area, with easily walkable restaurants. We ended up driving to beaches due to heat, but it would be fine to walk in cooler seasons. Siesta beach and all the other public accesses, most with free parking, are only minutes away by car. We would definitely stay again next time we are in Siesta Key!"
Sparkling Clean Villa at Vista Hermosa. Walk to Beach, Dining, Shopping & More 167
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

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Very nice hotel kind people"
Hudson 1-night trip
Posted 11 hours ago
DoubleTree by Hilton Sarasota Bradenton Airport

Find out more about Osprey

Find out more about Osprey

Osprey Villas information

Number of reviews
559
Accommodation
412 Villas
Lowest Price
NZ$1,675
Highest Price
NZ$1,675

Frequently asked questions

How much do villas in Osprey cost?
Villas in Osprey cost between NZ$1,675 and NZ$1,675 per night. These getaways provide the privacy to enjoy your own space at a price that won't stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Osprey?
Take your pick of 412 villas in Osprey. No matter if you're holidaying with the family or getting away with some friends, Expedia will help you find the best space for your whole crew.
What are the best cheap villas in Osprey?
Villas start at NZ$1,675 per night, so your Osprey adventure doesn't have to stretch your budget! Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is a pocket-friendly pick that comes with plenty of amenities, including a barbecue grill and a swimming pool. Island House Beach Resort V21 is another cheap stay in this sought-after destination. Amenities here include a barbecue grill and a swimming pool. If you're exploring Osprey on a budget, there are loads of popular and free attractions to add to your to-do list. Siesta Key Beach and Venice Beach are visitor favourites. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.