Osprey Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Osprey

2 bedrooms, Internet
Charming Florida Beach Home w King Bed Patio

Charming Florida Beach Home w King Bed Patio

2.0 star property
Bay Acres
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
United States
Alyssa
Charming Florida Beach Home w King Bed Patio
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5096)
"The room was clean and the staff was very nice."
United States
Jill
The price is HK$1,083
HK$1,400 total
includes taxes & fees
16 Nov - 17 Nov
Tropical Beach Resorts
Front of property – evening/night
Captiva Beach Resort

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1156)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
Sarasota
8.6 out of 10, Excellent, (2193)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Living area
SeaSpray Resort

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (67)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
The price is HK$1,802
HK$2,036 total
includes taxes & fees
17 Nov - 18 Nov
SeaSpray Resort
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (294)
"Fun place to stay for family vacation "
United States
Todd
The price is HK$2,635
HK$3,373 total
includes taxes & fees
30 Nov - 1 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club
Front of property
The Ringling Beach House

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (335)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House
Living area
Tiny House Siesta

Tiny House Siesta

2.0 star property
Sarasota
8.4 out of 10, Very good, (342)
"Enjoyable stay. "
United States
Lori
The price is HK$610
HK$1,634 total
includes taxes & fees
30 Nov - 1 Dec
Tiny House Siesta
Exterior
Kon Tiki Inn

Kon Tiki Inn

2.5 star property
Venice Island
10.0 out of 10, Exceptional, (243)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
The price is HK$1,172
HK$1,325 total
includes taxes & fees
18 Nov - 19 Nov
Kon Tiki Inn
On the beach, white sand
A Beach Retreat

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (572)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat
On the beach, white sand
Sea Club I Beach Resort

Sea Club I Beach Resort

3.0 star property
Longboat Key
9.2 out of 10, Wonderful, (331)
"Very nice beach themed bungalow. Loved the quiet and the views. "
United States
Jennifer
Sea Club I Beach Resort
Exterior
Siesta Key Island Rentals

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (49)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
United States
Julianna
Siesta Key Island Rentals
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
The price is HK$1,413
HK$2,028 total
includes taxes & fees
19 Nov - 20 Nov
The Inn On Siesta Key
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach

Tropical Villas of Venice Beach

3.5 star property
Venice Island
9.6 out of 10, Exceptional, (239)
"Nice unique property, room size was great, clean and comfortable. Liked that we had access to beach towels and equipment as well as laundry. "
United States
Rosa
Tropical Villas of Venice Beach
Garden
Siesta Palms By the Beach

Siesta Palms By the Beach

3.5 star property
South Village
9.4 out of 10, Exceptional, (136)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach
Exterior
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 star property
Bradenton
7.6 out of 10, Good, (53)
"Place was roomy and clean door lock was an issue had to call a couple of times to get it straighten out."
United States
rodger
Bradenton Apartments by Landing
Terrace/patio
Venice Beach Villas

Venice Beach Villas

3.0 star property
Venice Island
9.4 out of 10, Exceptional, (459)
"Always enjoy my stay here as it is close to everything. Friendly and helpful staff."
United States
Alicia
Venice Beach Villas
Property grounds
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (14)
"I don't care about tiki bars and pools, so this was great for me. beach access is a short walk, the unit was modern and clean. "
United States
Billie
The price is HK$612
HK$4,182 total
includes taxes & fees
17 Nov - 18 Nov
Chadwick Cove Resort & Marina
Outdoor pool, a heated pool
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Siesta Key Village
10.0 out of 10, Exceptional, (40)
"Very clean, new, close to downtown and the beach as well. Pool was the nicest we’ve seen, and the entire downstairs became a hangout all week for both kids and adults. Service from property manager Sarah was top notch!"
United States
Pete D.
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
On the beach, sun-loungers, beach towels
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key
9.8 out of 10, Exceptional, (79)
"Had a wonderful time at this condo. It was a great location and was kept very clean. The owner was very nice and helpful. Will definitely be back! "
United States
Karen
The price is HK$1,546
HK$3,040 total
includes taxes & fees
17 Nov - 18 Nov
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
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

Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key

10/10 Excellent
"Very friendly staff. Room was quite spacious and very clean."
Denise 1-night trip
Posted 3 days ago
Comfort Suites Sarasota - Siesta Key

Find out more about Osprey

Search for holiday rentals in Osprey on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

  • View our selection of featured holiday rentals in Osprey
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Look no further and take a look at our great range of rental properties in Osprey!

Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Osprey speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

What are some of the best holiday rentals that Osprey has to offer?

Charming Florida Beach Home w King Bed Patio: This highly rated holiday home rental in Osprey offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 35 Expedia holiday rentals, you're guaranteed to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Siesta Key Beach and Lido Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.