Osprey Holiday Rentals

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Holiday Rentals in Osprey

Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4356)
"We’ve stayed several times - always meets or exceeds expectations- very good value - thank you "
The price is AU$283
per night
30 May - 31 May
Tropical Beach Resorts
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, (1998)
"Lettie was very pleasant and helpful at checkin. Efficiency with a separate bedroom was spacious and clean. Good value for the price."
The price is AU$218
per night
27 May - 28 May
Hibiscus Suites - Gateway to Siesta Key
Sports facility
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (161)
"Great private access to the Siesta Key Beach. Large rooms with good amenities."
The price is AU$763
per night
28 May - 29 May
The Residences at Siesta Key Beach by Hyatt Vacation Club
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Florida Family Single | Private kitchen
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, (1038)
"The heated pool and the beach access."
The price is AU$331
per night
29 May - 30 May
Captiva Beach Resort
Aerial view
The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (246)
"Property was excellent and Robert Manager was very responsable !!!"
The Ringling Beach House
Beach
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
8.6 out of 10, Excellent, (27)
"We rented this house based upon the photos showing the vintage style beach home and because the location was literally steps away from where we were getting married on the beach. We had a minor mishap during our stay that was completely our fault. The owner was very responsive and understanding. I highly recommend this beautiful beach cottage."
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
Cabin (Tiny House - Yellow Lifeguard Stand) | Living area
Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (130)
"Came to siesta keys for the first time, really enjoyed our time there and it was a beautiful tiny place"
The price is AU$269
per night
30 May - 31 May
Tiny House Siesta
Exterior
Kon Tiki Inn
2.0 star property
10.0 out of 10, Exceptional, (110)
"all rooms were decorated with different themes clean "
The price is AU$225
per night
4 June - 5 June
Kon Tiki Inn
Outdoor pool, a heated pool
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
9.4 out of 10, Exceptional, (37)
"Nice time"
The price is AU$284
per night
28 May - 29 May
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, (191)
"They were so accommodating at Tropical Villas. As part of your stay you had beach chairs, beach umbrella, cooler, coffee pods, sand sifter, beach towels (all in your villa). On-site you have access to use bicycles and washer n dryer at no extra charge. The Elite Villa we stayed in had direct access to the enclosed bug free pool. Our room was extremly clean and reminiscent of old school Florida cottage. The grounds were lush and they even had a sweet little wild brown bunny who wondered around...
Tropical Villas of Venice Beach
On the beach, white sand
Sea Club I Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (279)
"The beach is beatiful on this Key. The Sea Beach is old but it was good for the price and right on the beach. We just needed a place to sleep so it was fine. No beach towels provided but they do have lounge chairs. On this key u have to Uber everywhere. Nothing is in walking distance."
Sea Club I Beach Resort
Beach nearby
Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking
8.8 out of 10, Excellent, (42)
"Conveniently located close to beach and village. However the area did get busy with public beach access nearby. Cute pool with outdoor shower but was also used by local kids. Unfortunately pest control treatment was scheduled during our stay and the guests upstairs had a domestic incident. But don’t let any of this deter you from booking. That was just our experience. The unit was perfect for a long weekend stay. Cleaning and maintenance people were very helpful and pleasant"
Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking
Beach nearby
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
7.8 out of 10, Good, (23)
"This is a great place to stay for a couple; the house is small but cozy. We really enjoyed our stay, and would consider staying here again. This is more like a 4.5 star rating. There were a few things that kept this from being a 5 star review: bathroom shower was incredibly small. Also the towel rack needed to be screwed in tighter, it was starting to come off the wall. Bathroom could also use a new paint job. The coffeemaker likely needs replacing..the inside of the reservoir looked pretty bad....
The price is AU$791
per night
27 May - 28 May
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
Property grounds
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach
9.8 out of 10, Exceptional, (27)
"I enjoyed my stay. Several years ago I stay in this tiny house and it was perfert for my stay."
The price is AU$289
per night
28 May - 29 May
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach
Beach nearby, white sand, sun-loungers, beach umbrellas
Siesta Palms By the Beach
3.5 star property
9.2 out of 10, Wonderful, (97)
"Our stay was wonderful, it was clean quiet and walking distance to beach. kitchen had all necessary utensils if needed.. liked the idea of beach chairs and beach wagon and cooler provided for use…..I would definitely stay again! "
Siesta Palms By the Beach
Smart TV
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
Outdoor pool, a heated pool
2 BR/2 BA Condo on Siesta Key
9.8 out of 10, Exceptional, (18)
"I traveled with my husband and 2 college aged kids and we were all very satisfied with our accommodations. Chris was very prompt responding to questions. The front desk staff was friendly and easy to work with. The condo space was great for four adults and provided everything we needed in the kitchen and beyond. The beach and pools were only a few minutes away and they did not disappoint. By far the best beach experience! We really liked the location too because it was close to the trolley stop...
2 BR/2 BA Condo on Siesta Key
Beach nearby, sun-loungers, beach towels
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
9.8 out of 10, Exceptional, (189)
"We really enjoyed our stay. We were so close to the beach, it being private was great. Chairs are available to bring down on the beach but you don’t have to bring them back which was awesome. Great communication. Would definitely stay again."
The price is AU$1,216
per night
17 June - 18 June
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
Beach nearby
SIESTA KEY BEACH , ROMANTIC UNIT C
9.0 out of 10, Wonderful, (17)
"Perfect location with a quick walk to the beach. Very clean, updated property. Excellent service. "
SIESTA KEY BEACH , ROMANTIC UNIT C
Beach
Siesta Key Beach House...................steps to main beach!!
Siesta Key Beach House...................steps to main beach!!
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See all available properties in Osprey
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.

Osprey Holiday Home Travel Info

Number of holiday homes
951
Popular accommodation
Osprey private holiday homes
Known landmarks
Siesta Key Beach, Venice Beach and Turtle Beach
International airports
Tampa, FL (TPA-Tampa Intl.) and Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)

Other types of properties in Osprey you may be interested in

Outdoor dining
Casey Key Resorts - Mainland
3.0 star property
8.4 out of 10, Very good, (1003)
"Everyone was very welcoming from the moment I got there till I checked out. They answered all my questions. The shuttle to the oceanfront property was wonderful and appreciated and it's complimentary. The shuttle driver was friendly and professional.I highly recommend this resort and I have plans to return."
The price is AU$267
per night
26 May - 27 May
Casey Key Resorts - Mainland
Lobby sitting area
Kompose Boutique Hotel
3.0 star property
9.0 out of 10, Wonderful, (3389)
"It was clean and safe. The only issue I had was the bathroom in the room. It was open. No privacy whatsoever. Other than that it was ok. "
The price is AU$141
per night
28 May - 29 May
Kompose Boutique Hotel
Outdoor pool, pool loungers
Hyatt Regency Sarasota
4.0 star property
8.0 out of 10, Very good, (1001)
"So beautiful and peaceful staff was very friendly."
The price is AU$231
per night
27 May - 28 May
Hyatt Regency Sarasota
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.

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 favourite 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 depend 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 AU$218 per night. Entering your travel dates in the search wizard might find you 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 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 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 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.

Recent reviews of Osprey properties
Expedia verified reviews

Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key

5/5 Excellent
"The Staff was Excellent!!!! Very Helpful with Dining Recommendations and Aleays Greeted us coming in or going out!. Clean and Comfy!"
A verified traveller stayed at Comfort Suites Sarasota - Siesta Key
Posted 18 hours ago
Comfort Suites Sarasota - Siesta Key