Holiday Rentals in Osprey

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Holiday Rentals in Osprey

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, 4,369 reviews
"This resort was a great place to stay. Literally walking distance to a beautiful beach. Beach chairs and umbrellas available for purchase, beach towels provided free of charge. The kitchenette at this property was stocked with everything we needed. Room was clean and comfortable. Front office staff did a super quick check in. They have a movie dvd collection for in room entertainment. It would be awesome if the TVs were updated to have streaming apps such as Netflix. I would definitely return to...
The price is €163
includes taxes & fees
3 Jun - 4 Jun
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, 2,004 reviews
"Very convenient for a big group The room was clean and the property has a great location close to siesta key you can even make it walking and also it’s close to restaurants and stores Just the pool needs a little bit of attention I think The rest was great"
The price is €133
includes taxes & fees
3 Jun - 4 Jun
Hibiscus Suites - Gateway to Siesta Key
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, 164 reviews
"The units are very spacious, clean and tastefully decorated. The pool is underwhelming as is the hot tub. Access to the beach was as advertised but losing the lounge chairs and umbrellas by 5:00 p.m.,hours before sunset is not ideal, especially for those with mobility issues who want to remain for the sunset, a highlight of the day. My children looked forward to paddle boarding and kayaking (as advertised) and inquired several times during our multiple day stay but were told none were available....
The price is €669
includes taxes & fees
19 Jun - 20 Jun
The Residences at Siesta Key Beach by Hyatt Vacation Club
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The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, 248 reviews
"Excelence!!!! The property, the area, the beach and the property manager was out of standing!!! We are very very pleased!!"
The Ringling Beach House
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, 1,040 reviews
"Would recommend this place to others. Good price for so close to the Siesta Key Beach. "
The price is €218
includes taxes & fees
3 Jun - 4 Jun
Captiva Beach Resort
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
8.6 out of 10, Excellent, 27 reviews
"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
Tiny House Siesta
2.0 star property
8.2 out of 10, Very good, 132 reviews
"Came to siesta keys for the first time, really enjoyed our time there and it was a beautiful tiny place"
The price is €164
includes taxes & fees
3 Jun - 4 Jun
Tiny House Siesta
Kon Tiki Inn
2.0 star property
10.0 out of 10, Exceptional, 114 reviews
"There was nothing to dislike about Kon Tiki. Property is well kept, very clean, updated and maintaince. "
The price is €137
includes taxes & fees
4 Jun - 5 Jun
Kon Tiki Inn
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
9.4 out of 10, Exceptional, 37 reviews
"Nice time"
The price is €175
includes taxes & fees
3 Jun - 4 Jun
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, 192 reviews
"The villa is well situated, being close to shopping, transport, and the tourist sites. We would definitely stay there again. The room have everything chair beach towels bikes kitchen staff love the place these was my second time Es un excelente lugar para gente mayor muy tranquilo aburrido para jóvenes .el room cuenta con todo es muy limpio y cómodo casa room tiene un patio con Barbie q hay bicicletas y el supermercado queda a 5 min lo mismo el centro "
Tropical Villas of Venice Beach
Sea Club I Beach Resort
3.0 star property
9.0 out of 10, Wonderful, 282 reviews
"The unit could use an update"
Sea Club I Beach Resort
Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking
8.8 out of 10, Excellent, 42 reviews
"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 Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
7.8 out of 10, Good, 23 reviews
"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 €490
includes taxes & fees
3 Jun - 4 Jun
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach
9.8 out of 10, Exceptional, 27 reviews
"I enjoyed my stay. Several years ago I stay in this tiny house and it was perfert for my stay."
The price is €179
includes taxes & fees
5 Jun - 6 Jun
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach
Sarasota Bay Dream
10.0 out of 10, Exceptional, 2 reviews
"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
Siesta Palms By the Beach
3.5 star property
9.2 out of 10, Wonderful, 99 reviews
"Stayed at Siesta Palms by the Beach for a week in May. The unit we had was spacious and very clean. Plenty of towels for our week stay. The shower was awesome!! It was also nice to have beach amenities to take with us such as chairs, umbrella, cart. However, the chairs were pretty rusted and old. Could use an update. The area was quiet and serene. Located in a quiet neighborhood and very close to beach access. However, once you reach the beach there isnt a lot of space for people to spread out...
Siesta Palms By the Beach
2 BR/2 BA Condo on Siesta Key
9.8 out of 10, Exceptional, 19 reviews
"Really enjoyed our stay. Condo was spacious and grounds were beautiful! Pool was awesome as well!"
2 BR/2 BA Condo on Siesta Key
SIESTA KEY BEACH , ROMANTIC UNIT C
9.0 out of 10, Wonderful, 17 reviews
"Perfect location with a quick walk to the beach. Very clean, updated property. Excellent service. "
SIESTA KEY BEACH , ROMANTIC UNIT C
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
9.8 out of 10, Exceptional, 190 reviews
"Steps to the beach, didn’t need our cars the entire time as there are free or for tip shuttles right off the main road always driving by. The village was extremely close only a 7min trolley ride. Home, bathrooms and beds were very clean. 3 full baths but showers were a bit tight for adults. Renter was very responsive and left some good tips in her book. Only real two small cons was the dryer was broken so we had to hang dry our laundry, and beach umbrella was missing a small piece which made it...
The price is €751
includes taxes & fees
17 Jun - 18 Jun
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
9.8 out of 10, Exceptional, 118 reviews
"Excellent vacation property right at the beautiful Siesta beach. We've rented both units, so we had the whole house and pool area all to ourselves. All details in the house are well though through, house is extremely clean and quiet. Large bedroms wth comfortable beds and plenty of common space in the front unit, smaller space in the back unit. Variety of food delivery options from restaurants in the area. The beach is short stroll away, my 82 yrs old mom was easily making the walk without her...
The price is €2,803
includes taxes & fees
16 Jun - 17 Jun
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
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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.

Other types of properties in Osprey you may be interested in

Casey Key Resorts - Mainland
3.0 star property
8.4 out of 10, Very good, 1,010 reviews
"Good"
The price is €200
includes taxes & fees
3 Jun - 4 Jun
Casey Key Resorts - Mainland
Kompose Boutique Hotel
3.0 star property
9.0 out of 10, Wonderful, 3,442 reviews
"It nice and quite"
The price is €103
includes taxes & fees
12 Jun - 13 Jun
Kompose Boutique Hotel
Hyatt Regency Sarasota
4.0 star property
8.2 out of 10, Very good, 1,008 reviews
"I enjoyed my stay at this hotel from the staff to the amenities, the pool, restaurant and the comfortable room. My only issue was the elevators. They were extremely slow and very small considering most people had luggage with them. Everything else was wonderful!"
The price is €197
includes taxes & fees
9 Jun - 10 Jun
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, apart-hotels, 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 favorite 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 depends 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 €133 per night. Entering your travel dates in the search wizard you might find 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.

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