Osprey Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Holiday Rentals in Osprey

Charming Florida Beach Home w King Bed Patio
2 bedrooms, Internet

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. "
Charming Florida Beach Home w King Bed Patio
Tropical Beach Resorts
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (5009)
"Great place and loved the closeness to the beach!"
The price is HK$1,184
HK$1,513 total
includes taxes & fees
1 Oct - 2 Oct
Tropical Beach Resorts
Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (1140)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort
SeaSpray Resort
Living area

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (43)
"Our stay was beautiful this hotel. Staff were very great. Customer service was great."
The price is HK$1,841
HK$2,080 total
includes taxes & fees
5 Oct - 6 Oct
SeaSpray Resort
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2178)
"Friendly staff, room was really clean!"
Hibiscus Suites - Gateway to Siesta Key
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (327)
"We liked the stay very much "
The Ringling Beach House
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Pool

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

9.8 out of 10, Exceptional, (24)
"Beatiful property, one block from the beach. Plenty of amenities"
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.2 out of 10, Wonderful, (327)
"Amazing place, it’s the perfect place for relax and enjoy the beach. I love and I will come back again and again."
Sea Club I Beach Resort
Tiny House Siesta
Living area

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (328)
"The location, size and price is just what we needed!"
The price is HK$616
HK$1,136 total
includes taxes & fees
2 Oct - 3 Oct
Tiny House Siesta
The Residences at Siesta Key Beach by Hyatt Vacation Club
Property amenity

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.6 out of 10, Exceptional, (290)
"We celebrated my daughter’s 30th birthday and it was perfect. I can’t wait to stay again. The beach was truly amazing. This place has everything you need. "
The price is HK$3,161
HK$3,967 total
includes taxes & fees
22 Oct - 23 Oct
The Residences at Siesta Key Beach by Hyatt Vacation Club
Bradenton Apartments by Landing
Exterior

Bradenton Apartments by Landing

4.5 star property
7.4 out of 10, Good, (45)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (132)
"We loved the condo. The distance to the beach was amazing. The wagon and beach chairs that were provided were so nice! The condo was clean and in great shape. The pool/ outdoor area was beautiful! We couldn’t have asked for a better place! "
Siesta Palms By the Beach
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (236)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
Kon Tiki Inn
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (445)
"I loved staying on the property. The unit was clean and walking distance to shopping, restaurants, a walking trail, and the beach! They also included all amenities you could possibly need!"
Venice Beach Villas
Private Home Directly on Siesta Key Beach!
On the beach

Private Home Directly on Siesta Key Beach!

9.8 out of 10, Exceptional, (6)
Private Home Directly on Siesta Key Beach!
Siesta Key Island Rentals
Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (48)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
Siesta Key Island Rentals
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach
The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On Siesta Key
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
On the beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (24)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views
On the beach, sun-loungers

Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

9.4 out of 10, Exceptional, (65)
"This is our second time staying here. Absolutely love this rental. Very clean and walking distance to the village "
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views
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

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"Yes"
Diane 1-night trip
Posted 1 day ago
Casey Key Resorts - Mainland

Find out more about Osprey

Find out more about Osprey

Search for holiday rentals in Osprey on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

  • View our selection of featured holiday rentals in Osprey
  • Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

Look no further and take a look at our great range of rental properties in Osprey!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Tropical Villas of Venice Beach: This holiday home rental outside of Osprey is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Osprey?

With 34 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.