Osprey Holiday Rentals

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Holiday Rentals in Osprey

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2074)
"Our suite was very clean and the hospitality was wonderful. Would definitely recommend to anyone. If we ever visit the area again we would definitely stay there."
The price is AU$304
includes taxes & fees
24 Nov - 25 Nov
Hibiscus Suites - Gateway to Siesta Key

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (211)
"This property is off the charts wonderful. Beautiful grounds, kind staff and incredible rooms. Loved every minute of our four night stay!"
The price is AU$721
includes taxes & fees
3 Dec - 4 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
Tropical Beach Resorts

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (179)
"Was a perfect option for our birthday visit and just a seashells throw away from the ocean. Was very nice and looking forward to another stay soon."
The price is AU$289
includes taxes & fees
6 Dec - 7 Dec
Tiny House Siesta

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (285)
"This was a lovely place. Just loved it. Will be back. "
The Ringling Beach House

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1057)
"Nice and quiet place, close to the beach and dining places."
Captiva Beach Resort

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (168)
"place is so cute and very clean and centrally located for what we needed. Shawn was great and would definately stay again. "
The price is AU$343
includes taxes & fees
3 Dec - 4 Dec
Kon Tiki Inn

SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B

8.6 out of 10, Excellent, (33)
"We were there when hurricane Debbie hit. Took down the fence and air conditioners. The owner was there within 30 minutes to have everything fixed. Other than that this is our happy place. We will be bsck"
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (217)
"Good location clean easy check in"
Tropical Villas of Venice Beach

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (298)
"Great property! Great front desk people! Beautiful beach!"
Sea Club I Beach Resort

Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

9.2 out of 10, Wonderful, (40)
"We arrived early and weren't able to check in early but the Ramada Inn staff were very accommodating. Offered us access to the pool and restaurant while we waited until the 4pm check in time. The food was great and and the staff were awesome! The only thing I wish I'd known was you can't fish from their docks."
The price is AU$288
includes taxes & fees
14 Dec - 15 Dec
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

2 BR/2 BA Condo on Siesta Key

9.8 out of 10, Exceptional, (33)
"This property doesn’t have a view of the Gulf, but it’s a mere .2 of mile walk before your toes hit the sand. Easy! Condo was super clean and the host was incredibly responsive to emails. I do wish more info was provided on well equipped it was. Didn’t realize there were coolers and a beach umbrella/tent we could use. We purchased a cabana. Bring your own beach towels. But overall an exceptional stay. Checking in was easy and they have a super friendly staff. "
2 BR/2 BA Condo on Siesta Key

WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US

10.0 out of 10, Exceptional, (114)
"Very nice. Clean "
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US

Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach

9.8 out of 10, Exceptional, (33)
"We really enjoyed our stay!.. Awesome tiny house,was just as described..We will certainly be back for future getaways!"
The price is AU$315
includes taxes & fees
24 Nov - 25 Nov
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach

Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking

8.6 out of 10, Excellent, (53)
"Property was an excellent location right beside the beach and plenty to do within walking distance. Perfect for a stay as a couple, plenty of space and good amenities. Fresh water outside to wash the sand off was a nice addition as well and much needed. We contacted the property management about possibly being able to enter the property about 20 minutes early and were told no, even though no one was working in or around the unit. So don't expect to be able to arrive a moment too early. My...
Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking

Vacation delight! Cozy condo just steps from the beach and St. Armands circle.

10.0 out of 10, Exceptional, (126)
"Very clean, had essentials and some you didnt think to bring like beach chairs, umbrellas, towels. Kitchen well stocked for cooking. Bathroom looked recently renovated. Quiet neighborhood. "
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.

Sarasota Bay Dream

10.0 out of 10, Exceptional, (2)
"This TT had 2 bedrooms and 2 baths. It also had a ‘jackknife’ sofa in the living room area. Water pressure in 2nd bathroom shower wasn’t as good as the master bedroom shower. We brought our own towels, washcloths to use only because there was no washer dryer in the TT, however there is coin operated machines in the campground. Owner supplied bedding, towels, some toiletries dishes, pots and pans, silverware, etc. all the stuff you would need for your stay. Had a few hiccups during our stay but...
Sarasota Bay Dream

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (313)
"Beautiful cottage with the perfect amount of space and amenities in a great location. Conveniently located down the street from the strip and right across the street from the beaches. Highly recommend to any couple whose looking to relax for the week"
Across The Street From #1 Beach

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (128)
"Upscale, very well kept condo with all the necessary items for a pleasant vacation. Quality towels and linen. Very clean and tastefully decorated. No clutter. Highly recommend."
Breathtaking Beach Front Property Ground Floor Condo

SIESTA KEY BEACH , ROMANTIC UNIT C

9.0 out of 10, Wonderful, (18)
"Communication at first was lost in translation with a bumpy start, but once all was figured out we hit the jackpot with this location. There were some beach chairs, towels and cooler available for us. We brought our own, but definitely appreciate having them if need be. With Florida weather it’s sunny one moment and pouring down rain the next, we appreciate that there were umbrellas also available for us. Shops and restaurants were within walking distance and the beach was literally across the...
SIESTA KEY BEACH , ROMANTIC UNIT C
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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Other types of properties in Osprey you may be interested in

Casey Key Resorts - Mainland

3.0 star property
8.6 out of 10, Excellent, (1085)
"Very kind staff"
The price is AU$250
includes taxes & fees
1 Dec - 2 Dec
Casey Key Resorts - Mainland

Hyatt Regency Sarasota

4.0 star property
8.2 out of 10, Very good, (1003)
"Very clean and upscale. All staff very courteous and friendly. "
The price is AU$339
includes taxes & fees
23 Dec - 24 Dec
Hyatt Regency Sarasota

Kompose Boutique Hotel

3.0 star property
9.0 out of 10, Wonderful, (3597)
"Very clean"
The price is AU$244
includes taxes & fees
1 Dec - 2 Dec
Kompose Boutique Hotel
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Nancy's Consignments, 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 28 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 Nancy's Consignments and Jim Neville Marine Preserve, 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.