Osprey Holiday Rentals

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Check prices for these dates

Tonight
2 Nov - 3 Nov
Tomorrow
3 Nov - 4 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Holiday Rentals in Osprey

2 bedrooms, Internet
Charming Florida Beach Home w King Bed Patio
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. "
United States
Alyssa
Charming Florida Beach Home w King Bed Patio
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5074)
"Clean room, great A/C, close to beach, very quiet, easy parking, close to restaurants, clean beach, very nice staff. "
United States
Marta
The price is S$266
includes taxes & fees
3 Nov - 4 Nov
Tropical Beach Resorts
Front of property – evening/night
Captiva Beach Resort
Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1152)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2188)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Living area
SeaSpray Resort
SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (59)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
The price is S$366
includes taxes & fees
3 Nov - 4 Nov
SeaSpray Resort
Front of property
The Ringling Beach House
The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (333)
"Miss Susan was great! Property was very clean! There was some water damage on the wall in the bathroom. Otherwise, wonderful property/stay! Steps to the beach! Well maintained. Would stay again for sure! "
United States
Sarah
The Ringling Beach House
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (293)
"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. "
United States
Tammy
The price is S$547
includes taxes & fees
2 Dec - 3 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club
Living area
Tiny House Siesta
Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (337)
"Excelente"
Mexico
Carlis
The price is S$266
includes taxes & fees
1 Dec - 2 Dec
Tiny House Siesta
On the beach, white sand
Sea Club I Beach Resort
Sea Club I Beach Resort
3.0 star property
9.2 out of 10, Wonderful, (330)
"Our room was on the beach! Beds and furniture were very comfortable!! Lots of outdoor seating and extremely close to the water!"
United States
Michelle
Sea Club I Beach Resort
Exterior
Kon Tiki Inn
Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (240)
"Great place to stay"
United States
Brad
The price is S$222
includes taxes & fees
18 Nov - 19 Nov
Kon Tiki Inn
Private kitchen
Siesta Key Island Rentals
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. "
United States
Julianna
The price is S$365
includes taxes & fees
3 Nov - 4 Nov
Siesta Key Island Rentals
Garden
Siesta Palms By the Beach
Siesta Palms By the Beach
3.5 star property
9.4 out of 10, Exceptional, (136)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key
The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (188)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
The price is S$307
includes taxes & fees
3 Nov - 4 Nov
The Inn On Siesta Key
Terrace/patio
Venice Beach Villas
Venice Beach Villas
3.0 star property
9.4 out of 10, Exceptional, (455)
"Always enjoy my stay here as it is close to everything. Friendly and helpful staff."
United States
Alicia
Venice Beach Villas
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach
Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, (239)
"Nice unique property, room size was great, clean and comfortable. Liked that we had access to beach towels and equipment as well as laundry. "
United States
Rosa
Tropical Villas of Venice Beach
Exterior
Bradenton Apartments by Landing
Bradenton Apartments by Landing
4.5 star property
7.6 out of 10, Good, (50)
"Place was roomy and clean door lock was an issue had to call a couple of times to get it straighten out."
United States
rodger
Bradenton Apartments by Landing
Property grounds
Chadwick Cove Resort & Marina
Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Nic place to stay and enjoy the area"
United States
isabel
The price is S$714
includes taxes & fees
11 Nov - 12 Nov
Chadwick Cove Resort & Marina
Private kitchen
Siesta Heron Suites & Villas
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is S$482
includes taxes & fees
10 Nov - 11 Nov
Siesta Heron Suites & Villas
Exterior
Paradise Cove at Lemon Bay
Paradise Cove at Lemon Bay
3.5 star property
8.2 out of 10, Very good, (79)
"Nice property and very inviting. I especially liked the dock."
United States
David
Paradise Cove at Lemon Bay
Outdoor pool
Longboat Bay Club
Longboat Bay Club
3.5 star property
10.0 out of 10, Exceptional, (1)
"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."
United States
Andrew
Longboat Bay Club
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

Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"All of the above was great!"
Ben 3-night trip
Posted 4 days ago
Lido Beach Resort

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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.