Osprey Vacation Rentals

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Check prices for these dates

Tonight
Nov 21 - Nov 22
Tomorrow
Nov 22 - Nov 23
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Osprey

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

Vacation Home in Bay Acres

2.0 star property
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

Aparthotel in South Village

3.5 star property
9.4 out of 10, Exceptional, (5106)
"The room was clean and the staff was very nice."
United States
Jill
The price is P7,463
P9,766 total
includes taxes & fees
Nov 30 - Dec 1
Tropical Beach Resorts
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

2.5 star property
8.6 out of 10, Excellent, (2196)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Front of property - evening/night
Captiva Beach Resort

Condo in South Village

3.0 star property
9.0 out of 10, Wonderful, (1160)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

3.5 star property
9.6 out of 10, Exceptional, (295)
"Loved our stay! "
United States
Michelle
The price is P19,986
P25,580 total
includes taxes & fees
Dec 8 - Dec 9
The Residences at Siesta Key Beach by Hyatt Vacation Club
Living area
SeaSpray Resort

Aparthotel in Siesta Key

4.0 star property
9.4 out of 10, Exceptional, (69)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
The price is P14,673
P16,581 total
includes taxes & fees
Dec 1 - Dec 2
SeaSpray Resort
Front of property
The Ringling Beach House

Apartment in Siesta Key

3.5 star property
9.0 out of 10, Wonderful, (336)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House
Living area
Tiny House Siesta

Mobile Home in Sarasota

2.0 star property
8.4 out of 10, Very Good, (342)
"Enjoyable stay. "
United States
Lori
The price is P6,305
P14,285 total
includes taxes & fees
Nov 27 - Nov 28
Tiny House Siesta
Exterior
Kon Tiki Inn

Aparthotel in Venice Island

2.5 star property
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 P9,600
P10,848 total
includes taxes & fees
Dec 15 - Dec 16
Kon Tiki Inn
On the beach, white sand
A Beach Retreat

Condo in Casey Key

2.5 star property
9.2 out of 10, Wonderful, (573)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat
Exterior
Siesta Key Island Rentals

Vacation Home in Siesta Key

3.0 star property
9.6 out of 10, Exceptional, (50)
"Very nice place, we loved it. Great location. "
United States
Derrick
The price is P7,551
P17,283 total
includes taxes & fees
Dec 3 - Dec 4
Siesta Key Island Rentals
On the beach, white sand
Sea Club I Beach Resort

Apartment in Longboat Key

3.0 star property
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
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

Cottage in Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (189)
"Great place to stay! "
United States
Carlos
The Inn On Siesta Key
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach

Vacation Home in Venice Island

3.5 star property
9.6 out of 10, Exceptional, (240)
"Great Location !!"
United States
Orleys
Tropical Villas of Venice Beach
Garden
Siesta Palms By the Beach

Aparthotel in South Village

3.5 star property
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

Aparthotel in Bradenton

4.5 star property
7.6 out of 10, Good, (54)
"Perfect place "
United States
chavelys
Bradenton Apartments by Landing
Terrace/patio
Venice Beach Villas

Condo in Venice Island

3.0 star property
9.4 out of 10, Exceptional, (460)
"Always enjoy my stay here as it is close to everything. Friendly and helpful staff."
United States
Alicia
Venice Beach Villas
Private kitchen
Siesta Heron Suites & Villas

Vacation Home in Siesta Key

3.5 star property
8.4 out of 10, Very Good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is P8,039
P20,937 total
includes taxes & fees
Nov 28 - Nov 29
Siesta Heron Suites & Villas
Property grounds
Chadwick Cove Resort & Marina

Condo in Manasota Key

4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is P4,855
P32,012 total
includes taxes & fees
Dec 1 - Dec 2
Chadwick Cove Resort & Marina
Exterior
Paradise Cove at Lemon Bay

Villa in Olde Englewood Village

3.5 star property
8.2 out of 10, Very Good, (80)
"Nice, quiet area. Private and had everything we needed! Very nice staff!! "
United States
Deb
Paradise Cove at Lemon Bay
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Everything was great."
Elsa 2-night trip
Posted 8 hours ago
Spark by Hilton Sarasota Siesta Key Gateway

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!

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Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Osprey?

Charming Florida Beach Home w King Bed Patio: Visitors give good reviews to this Osprey vacation home rental, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 35 Expedia vacation rentals, you're sure 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 like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.