Osprey Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Osprey

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4375)
"Staff was friendly. Room was great. Very comfortable at a great price. "
The price is CA $159
CA $210 total
includes taxes & fees
Jun 9 - Jun 10
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2006)
"Good location, room are very good and specious, nice appliances. "
The price is CA $174
CA $196 total
includes taxes & fees
Jun 5 - Jun 6
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, (165)
"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 CA $828
CA $989 total
includes taxes & fees
Jun 19 - Jun 20
The Residences at Siesta Key Beach by Hyatt Vacation Club
Save an average of 15% on thousands of hotels when you're signed in
The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (249)
"Excelence!!!! The property, the area, the beach and the property manager was out of standing!!! We are very very pleased!!"
The price is CA $437
CA $633 total
includes taxes & fees
Jun 6 - Jun 7
The Ringling Beach House
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, (1040)
"Would recommend this place to others. Good price for so close to the Siesta Key Beach. "
The price is CA $244
CA $322 total
includes taxes & fees
Jun 9 - Jun 10
Captiva Beach Resort
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
Tiny House Siesta
2.0 star property
8.2 out of 10, Very good, (134)
"We loved our tiny house! "
The price is CA $143
CA $254 total
includes taxes & fees
Jun 9 - Jun 10
Tiny House Siesta
Kon Tiki Inn
2.0 star property
10.0 out of 10, Exceptional, (115)
"There was nothing to dislike about Kon Tiki. Property is well kept, very clean, updated and maintaince. "
The price is CA $179
CA $203 total
includes taxes & fees
Jun 5 - Jun 6
Kon Tiki Inn
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
9.4 out of 10, Exceptional, (37)
"Nice time"
The price is CA $135
CA $253 total
includes taxes & fees
Jun 5 - Jun 6
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, (193)
"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
Sea Club I Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (283)
"Nice place for a quiet, short getaway "
Sea Club I Beach Resort
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 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 CA $150
CA $708 total
includes taxes & fees
Jun 17 - Jun 18
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)
"I enjoyed my stay. Several years ago I stay in this tiny house and it was perfert for my stay."
The price is CA $129
CA $258 total
includes taxes & fees
Jun 5 - Jun 6
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach
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
Siesta Palms By the Beach
3.5 star property
9.2 out of 10, Wonderful, (99)
"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)
"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)
"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)
"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 CA $544
CA $1,082 total
includes taxes & fees
Jun 18 - Jun 19
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)
"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 CA $2,080
CA $4,048 total
includes taxes & fees
Jun 16 - Jun 17
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
Don't see what you're looking for?
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 Vacation Rental Travel Info

Number of vacation rentals
951
Popular accommodation
Osprey private vacation 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

Casey Key Resorts - Mainland
3.0 star property
8.4 out of 10, Very good, (1013)
"Good"
The price is CA $234
CA $296 total
includes taxes & fees
Jun 5 - Jun 6
Casey Key Resorts - Mainland
Kompose Boutique Hotel
3.0 star property
9.0 out of 10, Wonderful, (3452)
"It is a beautiful eco friendly hotel, quite comfortable."
The price is CA $115
CA $149 total
includes taxes & fees
Jun 10 - Jun 11
Kompose Boutique Hotel
Hyatt Regency Sarasota
4.0 star property
8.2 out of 10, Very good, (1012)
"Bathroom is really small with a sulfer smell when you flush. "
The price is CA $217
CA $291 total
includes taxes & fees
Jun 9 - Jun 10
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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