Osprey Vacation Rentals

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Vacation Rentals in Osprey

Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4361)
"We’ve stayed several times - always meets or exceeds expectations- very good value - thank you "
The price is ￥23,922
￥30,579 total
includes taxes & fees
Jun 5 - Jun 6
Tropical Beach Resorts
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2003)
"The room and property was so clean. Front desk personnel was very friendly. "
The price is ￥18,960
￥21,425 total
includes taxes & fees
May 29 - May 30
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, (164)
"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 ￥95,329
￥113,929 total
includes taxes & fees
Jun 10 - Jun 11
The Residences at Siesta Key Beach by Hyatt Vacation Club
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Florida Family Single | Private kitchen | Fridge, microwave, coffee/tea maker, toaster
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, (1038)
"The heated pool and the beach access."
The price is ￥25,873
￥34,557 total
includes taxes & fees
May 29 - May 30
Captiva Beach Resort
Aerial view
The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (247)
"Excelence!!!! The property, the area, the beach and the property manager was out of standing!!! We are very very pleased!!"
The Ringling Beach House
Beach | On the 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 | Flat-screen TV, Netflix, streaming services
Tiny House Siesta
2.0 star property
8.2 out of 10, Very Good, (132)
"Came to siesta keys for the first time, really enjoyed our time there and it was a beautiful tiny place"
The price is ￥15,339
￥27,974 total
includes taxes & fees
May 29 - May 30
Tiny House Siesta
Exterior
Kon Tiki Inn
2.0 star property
10.0 out of 10, Exceptional, (114)
"The owners of Kon Tiki were both extremely nice and truly cared that everything was perfect for our stay. We had mentioned we were going to BBQ lobster and within minutes one of the owners was at the BBQ pit with everything we could need to BBQ. Our room was very clean with a small refrigerator, microwave and 2 top stove."
The price is ￥20,639
￥23,323 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥15,535
￥29,149 total
includes taxes & fees
May 29 - May 30
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, (281)
"The unit could use an update"
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 ￥17,261
￥81,330 total
includes taxes & fees
May 29 - May 30
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 ￥14,907
￥29,893 total
includes taxes & fees
Jun 2 - Jun 3
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key 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, white sand, sun loungers, beach umbrellas
Siesta Palms By the Beach
3.5 star property
9.2 out of 10, Wonderful, (98)
"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
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 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 ￥62,639
￥124,669 total
includes taxes & fees
Jun 17 - Jun 18
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
On the beach, sun loungers, beach umbrellas, beach towels
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
9.8 out of 10, Exceptional, (118)
"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 ￥239,567
￥466,305 total
includes taxes & fees
Jun 16 - Jun 17
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
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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.

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, (1000)
"Place was very clean as it always is, they are still renovating the rooms and they look great. Our only disappointments were dogs are supposed to be in the far back building and there was 1 in the main building and 2 different people actually had dogs out in the pool area where they aren't supposed to be and nobody said a word to them. Also there was a little league tournament over the weekend and there were alot of kids there raising hell in and out of the pool and the parents let them do...
The price is ￥25,084
￥31,746 total
includes taxes & fees
May 29 - May 30
Casey Key Resorts - Mainland
Lobby sitting area
Kompose Boutique Hotel
3.0 star property
9.0 out of 10, Wonderful, (3413)
"My stay at the hotel was excellent. The staff was always very friendly and attentive, which made my experience even more pleasant. Additionally, the facilities were spotlessly clean and well maintained. I would definitely recommend this hotel to anyone looking for a comfortable and friendly place to stay. "
The price is ￥15,064
￥19,150 total
includes taxes & fees
Jun 2 - Jun 3
Kompose Boutique Hotel
Outdoor pool, sun loungers
Hyatt Regency Sarasota
4.0 star property
8.0 out of 10, Very Good, (1005)
"Comfortable accommodations, clean and quiet. Great location, we had balcony room on high floor giving us great views"
The price is ￥24,166
￥32,627 total
includes taxes & fees
May 30 - May 31
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.

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Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Nancy's Consignments, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Osprey?

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

How many vacation rentals are there in Osprey?

With 31 Expedia vacation rentals, you're sure 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 like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.

Recent reviews of Osprey properties
Expedia verified reviews

Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key

5/5 Excellent
"Amazing!! The front desk lady was very nice and helpful "
A verified traveler stayed at Comfort Suites Sarasota - Siesta Key
Posted 12 hours ago
Comfort Suites Sarasota - Siesta Key