Osprey Holiday Rentals

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Our top choices for Osprey holiday rentals

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.4 out of 10, Exceptional, (13 reviews)
"Property was perfect for the price."
United States
William M.
The price is NZ$267
includes taxes & fees
1 Mar - 2 Mar
Charming cottage for 2 across warm mineral springs park

#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring
Warm Mineral Springs
9.0 out of 10, Wonderful, (12 reviews)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is NZ$285
includes taxes & fees
15 Mar - 16 Mar
#3 Small house walking distance to Warm Mineral Spring

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (351 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is NZ$386
includes taxes & fees
16 Feb - 17 Feb
Tiny House Siesta

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, (16 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is NZ$525
includes taxes & fees
1 Mar - 2 Mar
Nestled in North Port. Updated 2 Bed / 1 Bath.

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (60 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is NZ$516
includes taxes & fees
13 Feb - 14 Feb
Old Floridian cottage in Historic Gulf Village

Myakka River

Myakka River
Venice
9.8 out of 10, Exceptional, (18 reviews)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is NZ$757
includes taxes & fees
17 Feb - 18 Feb
Myakka River

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (254 reviews)
"Great place! "
United States
Michelle
The price is NZ$545
includes taxes & fees
16 Feb - 17 Feb
Kon Tiki Inn

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,299 reviews)
"Wonderful stay!"
United States
Victoria
The price is NZ$592
includes taxes & fees
18 Feb - 19 Feb
Tropical Beach Resorts

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (36 reviews)
"This is our 3rd year staying at this property. We love the location and convince of a quiet neighborhood off university road. We also appreciate the updated amenities and the bed topper is a huge plus for us! "
United States
Cecillia C.
The price is NZ$308
includes taxes & fees
11 Mar - 12 Mar
Beautiful University Pines Studio in Sarasota

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Bayshore Gardens
9.2 out of 10, Wonderful, (37 reviews)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
The price is NZ$286
includes taxes & fees
16 Feb - 17 Feb
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants

Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants
Manasota Key
9.8 out of 10, Exceptional, (30 reviews)
"We had a great time and a comfortable stay."
United States
Deb J.
Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants

Two Miles to Siesta Key

Two Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (45 reviews)
"Terry was a great host. The apartment was very comfortable and had everything we needed for our short stay in Sarasota. Would stay here again."
United States
Robert C.
The price is NZ$347
includes taxes & fees
11 Mar - 12 Mar
Two Miles to Siesta Key

Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
The price is NZ$1,184
includes taxes & fees
1 Mar - 2 Mar
Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (16 reviews)
"Great place and location "
United States
Cathy
The price is NZ$1,028
includes taxes & fees
15 Feb - 16 Feb
Chadwick Cove Resort & Marina

Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath
Bayou Oaks
9.2 out of 10, Wonderful, (43 reviews)
"Excellent place to stay"
United States
garry s.
The price is NZ$224
includes taxes & fees
4 Mar - 5 Mar
Riverside Oasis 1Bed/1Bath

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (70 reviews)
"We had an amazing stay! The pictures of the condo do not do it justice. The condo was clean and comfortable. There was plenty of space to keep everyone happy. The only downfall ( and not one that would keep us from returning ) is the parking. We drive a Tahoe and were unable to fit it in the assigned parking spot due to the pillars and actual property size. However they have a solution as there is an overflow lot they allow you to park in that is walkable! Don’t let this detour you as the condo...
United States
JENNA
The price is NZ$930
includes taxes & fees
19 Feb - 20 Feb
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (112 reviews)
"Simple old-school beach shack - so hard to find these days, absolutely loved it. Right on the water, best location along Nokomis Beach/Casey Key...short walk to restaurants also....absolutely fantastic."
United States
HAYLEY S.
The price is NZ$743
includes taxes & fees
17 Feb - 18 Feb
Casey Key Beachfront Escape: Charming 1BR Cottage

Home in quiet Bird Sanctuary Neighborhood, close to Beach

Home in quiet Bird Sanctuary Neighborhood, close to Beach
South Venice
9.6 out of 10, Exceptional, (16 reviews)
"The property was great and we love the area we hope we can rent this place again next year"
United States
Philip L.
The price is NZ$858
includes taxes & fees
28 Feb - 1 Mar
Home in quiet Bird Sanctuary Neighborhood, close to Beach

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$637
includes taxes & fees
25 Feb - 26 Feb
Siesta Key Village-Suite #1: A block to the Beach!

Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
10.0 out of 10, Exceptional, (62 reviews)
"The condo was very clean and the beach was very close."
United States
Rick C.
Renovated Beach Paradise. Ground Floor unit 64
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$379 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 Heron Suites & Villas: This holiday home rental outside of Osprey is located on the waterfront, and has an outdoor pool, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

How many holiday rentals are there in Osprey?

With 19 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.