Osprey Holiday Rentals

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Holiday Rentals in Osprey

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. "
The price is AU$362
includes taxes & fees
19 Jan - 20 Jan 2025
Tropical Beach Resorts

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (219)
"It exceeded our expectations. Perfect for a family stay with continental breakfast, spacious rooms, kitchen, pool, hot tub, and walk out to the beach with pool towels to use. "
The price is AU$966
includes taxes & fees
13 Jan - 14 Jan 2025
The Residences at Siesta Key Beach by Hyatt Vacation Club

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2078)
"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$291
includes taxes & fees
5 Jan - 6 Jan 2025
Hibiscus Suites - Gateway to Siesta Key

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1058)
"Nice and quiet place, close to the beach and dining places."
The price is AU$380
includes taxes & fees
30 Dec - 31 Dec
Captiva Beach Resort

Tiny House Siesta

2.0 star property
8.2 out of 10, Very good, (188)
"Had an amazing time away together. Quiet and peaceful and relaxing."
The price is AU$303
includes taxes & fees
12 Jan - 13 Jan 2025
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

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

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (300)
"My 4 night stay was beautiful and relaxing for the most part. Although, for being one of the few people residing there for a short vacation, I would've preferred that they hadn't put a rather noisey family right above me. It was startling and intrusive at times. "
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$397
includes taxes & fees
17 Jan - 18 Jan 2025
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (170)
"We stayed for one night and are very happy. Definitely we will return to stay. "
The price is AU$359
includes taxes & fees
30 Dec - 31 Dec
Kon Tiki Inn

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, (127)
"Sue worked very hard on restoring this property after the hurricanes. It was beautiful on the inside. It was very spacous with all new furnishings. The location is within walking distance to the beach, food, drinks, and shopping. The only downside was having to leave. We cannot recommend this place enough."
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.

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

10.0 out of 10, Exceptional, (116)
"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, (35)
"Located near restaurants and beaches. The place was clean, however the AC/heating unit was not working properly. We were there when it was cool and the heat did not work. We had contacted the host and maintenance personnel did come over, but seemed a little put out. Needless to say we did NOT have heat throughout our stay. "
The price is AU$330
includes taxes & fees
30 Dec - 31 Dec
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach

2 BR/2 BA Condo on Siesta Key

9.8 out of 10, Exceptional, (35)
"The beach is fabulous, the water pristine, the pool is beautiful and extremely helpful and knowledgeable staff. Highly recommend for sun and fun. Owner is very attentive and accommodating. Always replied to our questions in a timely manner"
2 BR/2 BA Condo on Siesta Key

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 Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (113)
"We absolutely loved our bungalow and Lisa was the best. Unfortunately hurricane Helene blessed us with a visit. We made the decision to stay since the eye was in the panhandle. Bad decision. Lisa made sure we were safe and moved us to another property on higher ground and made arrangements for us to get off the island the day after. Above and beyond. Thank you for everything!"
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (220)
"Beautiful Villas close to beach and shopping!"
Tropical Villas of Venice Beach

5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING

10.0 out of 10, Exceptional, (125)
"David was the property owner and easy to communicate with! We used both sides of this house- each side had its own kitchen and laundry! 6 bedrooms and plenty of outside deck space and a backyard pool. The beach chairs and umbrellas were a big help. We had everything we needed here for our Thanksgiving and wedding gathering. Thanks! The Arnold’s from Pittsburgh PA"
The price is AU$5,573
includes taxes & fees
1 Jan - 2 Jan 2025
5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

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, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!
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, (1079)
"Staff is nice if you approach them, but they do not go out of their way to talk to you. Standard 2 queen bed room with comfortable beds. The bathroom shower was new and nice, but the mirror and walls could use updating. Bathroom has dust in the corners and shelves. The location is very convenient to beaches and where we needed to be. Will return to take advantage of the pool, it looks amazing but weather was only in the 60s when we stayed."
The price is AU$346
includes taxes & fees
5 Jan - 6 Jan 2025
Casey Key Resorts - Mainland

Hyatt Regency Sarasota

4.0 star property
8.2 out of 10, Very good, (1007)
"Good pet friendly hotel"
The price is AU$394
includes taxes & fees
20 Jan - 21 Jan 2025
Hyatt Regency Sarasota

Kompose Boutique Hotel

3.0 star property
9.0 out of 10, Wonderful, (3593)
"Super clean rooms, 24/7 front desk and snacks (for purchase) available. Fast & friendly check-in, all around great solid stay. It is close to Ringling & itsbnice to take a walk there because it’s gorgeous & depending on the time there are dining options too. "
The price is AU$259
includes taxes & fees
7 Jan - 8 Jan 2025
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.

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 26 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. Oscar Scherer State Park and Historic Spanish Point are other places to visit while you're in town.

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.