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, (276 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
The price is NZ$217
includes taxes & fees
1 June - 2 June
Kon Tiki Inn

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
The price is NZ$563
includes taxes & fees
19 May - 20 May
Cedar Run Resort - Roam Hospitality

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,481 reviews)
"Loved our stay, room was beautiful and bed was so comfy! So close to the beach, perfect location. Would definitely stay again!"
United States
Amberly
The price is NZ$349
includes taxes & fees
20 May - 21 May
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,309 reviews)
"Excellent location, great place to stay! "
United States
Lynn
The price is NZ$304
includes taxes & fees
18 May - 19 May
Hibiscus Suites - Gateway to Siesta Key

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (633 reviews)
"Love this place"
United States
Marialis
The price is NZ$377
includes taxes & fees
18 May - 19 May
A Beach Retreat

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is NZ$1,635
includes taxes & fees
30 May - 31 May
Gulf View Condominiums

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is NZ$972
includes taxes & fees
15 May - 16 May
Chadwick Cove Resort & Marina

Minorga Sand Dollar on the Key

Minorga Sand Dollar on the Key
3.5 star property
Siesta Key Village
The price is NZ$917
includes taxes & fees
20 May - 21 May
Minorga Sand Dollar on the Key

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (368 reviews)
"Close to the beach"
United States
Stephen
The Ringling Beach House

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,250 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
The price is NZ$451
includes taxes & fees
17 May - 18 May
Captiva Beach Resort

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (366 reviews)
"Cute place perfect for our holiday beach stay."
United States
Shelly
The price is NZ$392
includes taxes & fees
17 May - 18 May
Tiny House Siesta

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (274 reviews)
"Great place"
United States
tony
The price is NZ$370
includes taxes & fees
21 May - 22 May
Casey Key Resort - Gulf Shores

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 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$784
includes taxes & fees
20 May - 21 May
The Inn On Siesta Key

5 Mi to Riverwalk: Bradenton Family Home w/ Yard

5 Mi to Riverwalk: Bradenton Family Home w/ Yard
3.0 star property
Bayshore Gardens
5 Mi to Riverwalk: Bradenton Family Home w/ Yard

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (42 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is NZ$560
includes taxes & fees
19 May - 20 May
Siesta Heron Suites & Villas

FANCY RETREREAT

FANCY RETREREAT
3.0 star property
Bradenton
The price is NZ$1,084
includes taxes & fees
26 May - 27 May
FANCY RETREREAT

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
The price is NZ$948
includes taxes & fees
18 May - 19 May
Sarasota Family Home Private Heated Pool Relax

Siesta Sands Beach Resort 4th Floor With Elevator

Siesta Sands Beach Resort 4th Floor With Elevator
3.5 star property
South Village
The price is NZ$1,359
includes taxes & fees
21 May - 22 May
Siesta Sands Beach Resort 4th Floor With Elevator

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (125 reviews)
"Enjoyed our stay great location easy walk to village and the beach"
United States
Gregory
The price is NZ$553
includes taxes & fees
27 May - 28 May
SeaSpray Resort

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is NZ$1,991
includes taxes & fees
19 May - 20 May
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$217 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 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 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 16 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.