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Osprey Holiday Rentals

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Our top choices for Osprey holiday rentals

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (288 reviews)
"Great place to stay!!!"
United States
Tara
The price is NZ$220
includes taxes & fees
29 June - 30 June
Kon Tiki Inn

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,351 reviews)
"great place to stay for a couple of nights. "
United States
Diana
The price is NZ$298
includes taxes & fees
29 June - 30 June
Hibiscus Suites - Gateway to Siesta Key

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,605 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is NZ$351
includes taxes & fees
30 June - 1 July
Tropical Beach Resorts

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (144 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is NZ$536
includes taxes & fees
20 July - 21 July
SeaSpray Resort

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (370 reviews)
"Loved the tiny house will stay there again!"
United States
Nydia
The price is NZ$354
includes taxes & fees
30 June - 1 July
Tiny House Siesta

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (644 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is NZ$407
includes taxes & fees
29 June - 30 June
A Beach Retreat

Secluded Cottage - Private BBQ Deck Firepit

Secluded Cottage - Private BBQ Deck Firepit
2.0 star property
Sarasota
Secluded Cottage - Private BBQ Deck Firepit

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
8.8 out of 10, Excellent, (5 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is NZ$1,110
includes taxes & fees
30 June - 1 July
Cedar Run Resort - Roam Hospitality

The Ashton Hideaway

The Ashton Hideaway
2.0 star property
Sarasota
The Ashton Hideaway

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,271 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is NZ$360
includes taxes & fees
6 July - 7 July
Captiva Beach Resort

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (277 reviews)
"Is was a great place to stay, everything was perfect!"
United States
Tracie Costello
The price is NZ$368
includes taxes & fees
9 July - 10 July
Casey Key Resort - Gulf Shores

Waterfront Luxury Remodeled Studio! Pool Tiki Bar

Waterfront Luxury Remodeled Studio! Pool Tiki Bar
3.0 star property
Whitfield Estates
The price is NZ$381
includes taxes & fees
29 June - 30 June
Waterfront Luxury Remodeled Studio! Pool Tiki Bar

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (69 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is NZ$612
includes taxes & fees
30 June - 1 July
Siesta Key Island Rentals

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is NZ$604
includes taxes & fees
29 June - 30 June
Siesta Heron Suites & Villas

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is NZ$678
includes taxes & fees
30 June - 1 July
The Inn On Siesta Key

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is NZ$967
includes taxes & fees
6 July - 7 July
Chadwick Cove Resort & Marina

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is NZ$1,651
includes taxes & fees
12 July - 13 July
Gulf View Condominiums

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
The price is NZ$966
includes taxes & fees
29 June - 30 June
Sarasota Family Home Private Heated Pool Relax

Lulu's Crescent Cottage #2

Lulu's Crescent Cottage #2
2.5 star property
Siesta Key
The price is NZ$1,143
includes taxes & fees
27 July - 28 July
Lulu's Crescent Cottage #2

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is NZ$1,790
includes taxes & fees
30 June - 1 July
Siesta Heron 7
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

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, 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 NZ$220 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. 

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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 lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

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

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

How many holiday rentals are there in Osprey?

With 13 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 Venice 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.