Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Osprey

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

Charming Florida Beach Home w King Bed Patio

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. "
Charming Florida Beach Home w King Bed Patio
Tropical Beach Resorts
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (5005)
"A great little hotel, the beach is beautiful too, will be back, this is our 3rd year coming."
The price is NT$4,255
NT$5,498 total
includes taxes & fees
Sep 29 - Sep 30
Tropical Beach Resorts
Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (1140)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort
SeaSpray Resort
Deluxe Suite, 2 Bedrooms | Living area

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (43)
"Our stay was beautiful this hotel. Staff were very great. Customer service was great."
The price is NT$6,990
NT$7,898 total
includes taxes & fees
Sep 29 - Sep 30
SeaSpray Resort
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2178)
"Friendly staff, room was really clean!"
Hibiscus Suites - Gateway to Siesta Key
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (326)
"We liked the stay very much "
The Ringling Beach House
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.2 out of 10, Wonderful, (326)
"Amazing place, it’s the perfect place for relax and enjoy the beach. I love and I will come back again and again."
Sea Club I Beach Resort
Tiny House Siesta
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (328)
"The location, size and price is just what we needed!"
The price is NT$2,417
NT$4,456 total
includes taxes & fees
Sep 30 - Oct 1
Tiny House Siesta
The Residences at Siesta Key Beach by Hyatt Vacation Club
Property amenity

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.6 out of 10, Exceptional, (290)
"We celebrated my daughter’s 30th birthday and it was perfect. I can’t wait to stay again. The beach was truly amazing. This place has everything you need. "
The price is NT$12,401
NT$15,565 total
includes taxes & fees
Oct 22 - Oct 23
The Residences at Siesta Key Beach by Hyatt Vacation Club
Bradenton Apartments by Landing
Exterior

Bradenton Apartments by Landing

4.5 star property
7.4 out of 10, Good, (45)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.4 out of 10, Exceptional, (131)
"We loved the condo. The distance to the beach was amazing. The wagon and beach chairs that were provided were so nice! The condo was clean and in great shape. The pool/ outdoor area was beautiful! We couldn’t have asked for a better place! "
Siesta Palms By the Beach
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (235)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
Kon Tiki Inn
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (445)
"I loved staying on the property. The unit was clean and walking distance to shopping, restaurants, a walking trail, and the beach! They also included all amenities you could possibly need!"
Venice Beach Villas
Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (48)
"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. "
Siesta Key Island Rentals
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach
The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On Siesta Key
Paradise Cove at Lemon Bay
Exterior

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
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very Good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas
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

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"All was excellent 👍"
Elvin 1-night trip
Posted 1 day ago
Hyatt Place Sarasota/Bradenton Airport

Find out more about Osprey

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
  • Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

Look no further and take a look at our great range of rental properties in Osprey!

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?

Tropical Villas of Venice Beach: This vacation home rental near Osprey is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Osprey?

With 34 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.