Holiday Rentals in Osprey

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Holiday 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. "
Charming Florida Beach Home w King Bed Patio

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (5023)
"Great place and loved the closeness to the beach!"
The price is €142
includes taxes & fees
19 Oct - 20 Oct
Tropical Beach Resorts

Captiva Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (1141)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2179)
"Friendly staff, room was really clean!"
Hibiscus Suites - Gateway to Siesta Key

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (46)
"I love everything about this place so beautiful with walking distance to the beach "
The price is €200
includes taxes & fees
20 Oct - 21 Oct
SeaSpray Resort

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (327)
"We liked the stay very much "
The Ringling Beach House

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (291)
"Loved our stay! "
The price is €450
includes taxes & fees
23 Oct - 24 Oct
The Residences at Siesta Key Beach by Hyatt Vacation Club

Sea Club I Beach Resort

3.0 star property
9.2 out of 10, Wonderful, (327)
"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

2.0 star property
8.4 out of 10, Very good, (329)
"Clean space, with nice private patio. Excellent location! Plenty of eating options around. Will definitely stay at these Tiny Homes again!"
The price is €98
includes taxes & fees
9 Oct - 10 Oct
Tiny House Siesta

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

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (132)
"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

Bradenton Apartments by Landing

4.5 star property
7.6 out of 10, Good, (46)
"Perfect place "
Bradenton Apartments by Landing

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (237)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
The price is €135
includes taxes & fees
9 Oct - 10 Oct
Kon Tiki Inn

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (448)
"Staff was great. Room was very clean. Laundry onsite and the pool was wonderful! Will stay again!!!"
Venice Beach Villas

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 €310
includes taxes & fees
9 Oct - 10 Oct
Siesta Key Island Rentals

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (184)
"clean and close proximity to beach and restaurants"
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

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

10.0 out of 10, Exceptional, (40)
"This was the perfect place to stay for a large family with kids. The location to the beach and restaurants couldn't have been more convenient. Amazing vacation!"
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Private Home Directly on Siesta Key Beach!

9.8 out of 10, Exceptional, (6)
"The home was beautiful and well equipped and management was quick to respond to any questions that we had. Direct access to a gorgeous beach was definitely the highlight!! "
Private Home Directly on Siesta Key Beach!

Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

9.4 out of 10, Exceptional, (35)
"Great location and experience"
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
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

Find out more about Osprey

Find out more about Osprey

Everything you need to know about Osprey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osprey holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey holiday rentals we have selected for you start as low as €98 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 holiday 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 holiday.

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 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 34 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.