Osprey Holiday Rentals

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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. "
The price is NZ$556
includes taxes & fees
29 July - 30 July
Charming Florida Beach Home w King Bed Patio

Relaxing 2BR Florida Home Close to Beach

2.0 star property
The price is NZ$605
includes taxes & fees
24 July - 25 July
Relaxing 2BR Florida Home Close to Beach

2BR Oasis with a Cozy Lanai 5 Min to Nokomis Beach

8.0 out of 10, Very good, (2)
"Everything was lovely, just as described. The only problem was the ant problem in the kitchen. "
2BR Oasis with a Cozy Lanai 5 Min to Nokomis Beach

2BR Florida Home Near the Shore!

6.8 out of 10, (3)
"Had an odor. Property by major roadway. Other than than it was good"
2BR Florida Home Near the Shore!

Perfect Getaway with the pool

10.0 out of 10, Exceptional, (25)
"We enjoyed our stay very much. Will stay again"
The price is NZ$608
includes taxes & fees
4 Aug - 5 Aug
Perfect Getaway with the pool

Escape to a Pool Home on a Lake

2.0 star property
The price is NZ$1,411
includes taxes & fees
17 Aug - 18 Aug
Escape to a Pool Home on a Lake

Relaxation Awaits: Luxurious Vacation Home with Heated Pool near Mineral Springs

2.0 star property
10.0 out of 10, Exceptional, (4)
"We needed a place to shelter from the hurricane for a few days. This home is beautiful, comfortable and has everything we needed. Communication with the owner was extremely easy. Would definitely stay again. "
The price is NZ$906
includes taxes & fees
24 July - 25 July
Relaxation Awaits: Luxurious Vacation Home with Heated Pool near Mineral Springs

New Two story Cozy House Near Warm Mineral Springs

10.0 out of 10, Exceptional, (15)
"Had an awesome with friends and family and will stay again if we’re in the area."
The price is NZ$720
includes taxes & fees
28 July - 29 July
New Two story Cozy House Near Warm Mineral Springs

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

10.0 out of 10, Exceptional, (7)
"We enjoyed our stay! The place was well-decorated, very clean, & overall comfortable. Hosts were very responsive as well!"
The price is NZ$351
includes taxes & fees
27 July - 28 July
Nestled in North Port. Updated 2 Bed / 1 Bath.

Myakka River

9.8 out of 10, Exceptional, (18)
"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 "
The price is NZ$732
includes taxes & fees
24 July - 25 July
Myakka River

Charming 2-bedroom house in Englewood with WiFi and AC

The price is NZ$402
includes taxes & fees
24 July - 25 July
Charming 2-bedroom house in Englewood with WiFi and AC

1.3 Acres PETS Waterfront FUN! Caged/Heated Pool, 100' Pier, CANOES Kayaks incl!

9.4 out of 10, Exceptional, (81)
"We enjoyed the spacious house, heated pool, large backyard, fishing pier, kayaks for use, and close proximity to many beaches, parks and walking paths, pickleball courts, restaurants, breweries, farmers market, shopping.We stayed 4 weeks and had plenty of room for family one week and friends another week. The beds were very comfortable. Thanks!"
The price is NZ$759
includes taxes & fees
3 Aug - 4 Aug
1.3 Acres PETS Waterfront FUN! Caged/Heated Pool, 100' Pier, CANOES Kayaks incl!

120 steps to beach! Safely on the beach side of the road!

9.8 out of 10, Exceptional, (177)
"House was nice and had great location!"
The price is NZ$738
includes taxes & fees
28 July - 29 July
120 steps to beach! Safely on the beach side of the road!

Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!

9.2 out of 10, Wonderful, (47)
"Very nice place on the beach"
Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!

Majestic Sunsets on the Beach just 50 steps away + 2 King beds

10.0 out of 10, Exceptional, (27)
"really enjoyed the rental. the decor was great the location was perfect for us. had everything we needed "
Majestic Sunsets on the Beach just 50 steps away + 2 King beds

Mimosa Memories

9.4 out of 10, Exceptional, (27)
"The property is somewhat aged but everything is clean, and any issues were addressed promptly and to our complete satisfaction. It is an excellent location. Easy to get to and on a very quiet street. We would be more than happy to stay at this location again."
The price is NZ$529
includes taxes & fees
24 July - 25 July
Mimosa Memories

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

9.2 out of 10, Wonderful, (55)
"Loved our stay! "
The price is NZ$589
includes taxes & fees
2 Aug - 3 Aug
Gorgeous Pool house 5 min from the beach, shopping and restaurants I

Renovated Quiet Venice Pool + Hot Tub Oasis-1/1!

9.2 out of 10, Wonderful, (15)
"The space was as advertised, clean and just the right size for us. Despite colder than normal temperatures, we had a great getaway and really enjoyed the hot tub."
The price is NZ$414
includes taxes & fees
6 Aug - 7 Aug
Renovated Quiet Venice Pool + Hot Tub Oasis-1/1!

"Venice Oasis: Beach-Ready Retreat!"

2.0 star property
10.0 out of 10, Exceptional, (4)
"In short this property is perfectly set up for anybody! The thought and care that is instantly obvious upon arrival is something special! Best 4th of July weekend ever!!"
The price is NZ$647
includes taxes & fees
1 Aug - 2 Aug
"Venice Oasis: Beach-Ready Retreat!"

Modern 2 Bedroom Farmhouse

9.2 out of 10, Wonderful, (7)
"Would highly recommend for a one or two night stay"
The price is NZ$580
includes taxes & fees
24 July - 25 July
Modern 2 Bedroom Farmhouse
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

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?

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 31 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.