Osprey Vacation Rentals

Start date: Check-in selected.
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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Rentals in Osprey

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. "
The price is CA $173
CA $440 total
includes taxes & fees
Sep 11 - Sep 12
Charming Florida Beach Home w King Bed Patio

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4969)
"A great little hotel, the beach is beautiful too, will be back, this is our 3rd year coming."
The price is CA $193
CA $249 total
includes taxes & fees
Sep 11 - Sep 12
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2171)
"Bed comfort , great location, friendly staff. "
The price is CA $156
CA $176 total
includes taxes & fees
Sep 11 - Sep 12
Hibiscus Suites - Gateway to Siesta Key

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1129)
"2nd time and excellent as always..close to the beach and great surroundings "
The price is CA $195
CA $244 total
includes taxes & fees
Sep 11 - Sep 12
Captiva Beach Resort

SeaSpray Resort

4.0 star property
9.6 out of 10, Exceptional, (37)
"I love everything about this place so beautiful with walking distance to the beach "
The price is CA $317
CA $358 total
includes taxes & fees
Sep 14 - Sep 15
SeaSpray Resort

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (321)
"Its a nice little family spot"
The Ringling Beach House

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

9.8 out of 10, Exceptional, (24)
"Beatiful property, one block from the beach. Plenty of amenities"
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Sea Club I Beach Resort

3.0 star property
9.2 out of 10, Wonderful, (322)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (323)
"The location, size and price is just what we needed!"
The price is CA $110
CA $202 total
includes taxes & fees
Sep 12 - Sep 13
Tiny House Siesta

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (128)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (44)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (229)
"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"
Kon Tiki Inn

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.6 out of 10, Exceptional, (288)
"Great beach front property with amenities"
The price is CA $547
CA $689 total
includes taxes & fees
Sep 29 - Sep 30
The Residences at Siesta Key Beach by Hyatt Vacation Club

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. "
The price is CA $148
CA $372 total
includes taxes & fees
Sep 11 - Sep 12
Siesta Key Island Rentals

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (5)
Private Home Directly on Siesta Key Beach!

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (436)
"Clean and welcoming property"
Venice Beach Villas

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

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (21)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

9.4 out of 10, Exceptional, (64)
"This is our second time staying here. Absolutely love this rental. Very clean and walking distance to the village "
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Osprey Hotel Reviews

Find out more about Osprey

Find out more about Osprey

Everything you need to know about Osprey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osprey vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey vacation rentals we have selected for you start as low as CA $110 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osprey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 30 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.