Osprey Holiday Rentals

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Our top choices for Osprey holiday rentals

Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$753
includes taxes & fees
27 Apr - 28 Apr
Sunny Coastal Escape

Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
The price is NZ$743
includes taxes & fees
27 Apr - 28 Apr
Charming Osprey Home

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (359 reviews)
"super clean and comfortable. we were 4 people and had a very comfortable and lovely stay. i felt super at home and the location is very centralized to everything "
United States
Adanna
The price is NZ$423
includes taxes & fees
12 Apr - 13 Apr
Tiny House Siesta

5 Mi to Golf & Trails: North Port Retreat w/ Pool

5 Mi to Golf & Trails: North Port Retreat w/ Pool
3.0 star property
North Port
10.0 out of 10, Exceptional, (1 review)
"The house had everything we needed, great location & neighborhood also."
United States
Gina
5 Mi to Golf & Trails: North Port Retreat w/ Pool

#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring
Warm Mineral Springs
9.2 out of 10, Wonderful, (13 reviews)
"My favorite place to stay when I come to visit my aunt! It’s comfy, clean and perfect location! I’ll be booking again in June. This was my 4 stay I think! You have all you need, and a quiet location. It truly is a gem! "
United States
BABS G.
The price is NZ$290
includes taxes & fees
31 Mar - 1 Apr
#3 Small house walking distance to Warm Mineral Spring

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is NZ$548
includes taxes & fees
1 Apr - 2 Apr
Old Floridian cottage in Historic Gulf Village

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (19 reviews)
"Property was perfect for the price."
United States
William M.
The price is NZ$271
includes taxes & fees
5 Apr - 6 Apr
Charming cottage for 2 across warm mineral springs park

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (37 reviews)
"Nice house. Very clean. Comfortable bed and linens. Easy check in and out. Convenient location "
United States
Kelly
The price is NZ$586
includes taxes & fees
5 Apr - 6 Apr
Mimosa Memories

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (20 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is NZ$430
includes taxes & fees
31 Mar - 1 Apr
Nestled in North Port. Updated 2 Bed / 1 Bath.

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Sabal Harbour
10.0 out of 10, Exceptional, (29 reviews)
"Everything was great!"
United States
Lisa and Colin M.
The price is NZ$640
includes taxes & fees
21 Apr - 22 Apr
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (264 reviews)
"Very nice rooms and close to everything. Owner is very welcoming."
United States
Jennifer
The price is NZ$254
includes taxes & fees
7 Apr - 8 Apr
Kon Tiki Inn

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (29 reviews)
"Clean and great location! Would stay again! "
United States
Laura W.
The price is NZ$631
includes taxes & fees
31 Mar - 1 Apr
[escape to paradise] siesta key beach getaway

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (39 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
The price is NZ$345
includes taxes & fees
30 Mar - 31 Mar
Beautiful University Pines Studio in Sarasota

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
The price is NZ$936
includes taxes & fees
31 Mar - 1 Apr
Direct Beachfront 2BR Cottage on Casey Key!

Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (113 reviews)
"Gorgeous view and comfortable interior. Great beach access and good pool. "
United States
Tanya M.
Sunset and beach view from your balcony Unit 403

Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG

Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG
South Bradenton
Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG

Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.

Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.
Nokomis
9.4 out of 10, Exceptional, (36 reviews)
"Our stay was lovely and beautiful l. Everything was nice and clean and anywhere we went was only 5 minutes away so the location and neighborhood was great! "
United States
Chelsey H.
Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.

Waterfront Getaway, a Boating Paradise

Waterfront Getaway, a Boating Paradise
Englewood
10.0 out of 10, Exceptional, (52 reviews)
"Always an amazing stay"
United States
christine w.
The price is NZ$600
includes taxes & fees
6 Apr - 7 Apr
Waterfront Getaway, a Boating Paradise

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (181 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
The price is NZ$679
includes taxes & fees
14 Apr - 15 Apr
Paradise Retreat with HEATED POOL-- Need We Say More

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (45 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
The price is NZ$799
includes taxes & fees
30 Mar - 31 Mar
Siesta Key Village-Suite #1: A block to the Beach!
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$254 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?

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 17 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.