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Compare 253 Cottages in Osprey with updated reviews, rates, and availability.

Across The Street From #1 Beach
Speaks For Itself. No Stress Here!

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (313)
"Beautiful cottage with the perfect amount of space and amenities in a great location. Conveniently located down the street from the strip and right across the street from the beaches. Highly recommend to any couple whose looking to relax for the week"
Across The Street From #1 Beach
The Inn On Siesta Key
Outdoor pool

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (164)
"Such a beautiful week maintained property with every thing you could possibly need or want to enjoy the area. ♥️"
The Inn On Siesta Key
Country Cottage Home
Welcome to the Country Cottage

Country Cottage Home

9.6 out of 10, Exceptional, (119)
"We came in town for a weekend at the Freedom Factory Track. Easy commute, easy stay. Just as describes. "
Country Cottage Home
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Beach

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (50)
"This place was exactly as described. Cute little cottage with an ocean view. We loved waking up to hearing the ocean and watching the dolphins pass through every day. Beach is loaded with beautiful shells. We had a maintenance issue but the owner was extremely helpful had it taken care immediately "
The price is AED 1,462
AED 2,704 total
includes taxes & fees
28 Nov - 29 Nov
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Heated Pool, Beach and Amenities, 2-3 min walk.
Outdoor dining

Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (65)
"Very clean, nice location, close to beach and pool, can use the trolley. Quaint duplex with lots of charm. Four adults stayed here with no problems. Would rent again."
Heated Pool, Beach and Amenities, 2-3 min walk.
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
Charming Guesthouse

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

10.0 out of 10, Exceptional, (102)
"We were celebrating my nephew's girlfriend's 21 birthday. The house was amazing. It was clean and had everything we needed. Kathy was so nice and helpful. We were less than 2 miles from the beach. The beds were comfortable, the decor was beach themed and very relaxing. I will be staying here again."
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
Mermaid Cottage
Exterior detail

Mermaid Cottage

10.0 out of 10, Exceptional, (5)
"My brother and I visited my aunt in Sarasota. Mermaid Cottage was a perfect location. It’s in a lovely neighborhood and is close to both the airport and the beach. The cottage is very clean and well appointed. Our host was very responsive when we couldn’t figure out how to lock the front door! Overall just a great experience. We will be back! Thank you!"
Mermaid Cottage
NEW: Free standing Cottage within steps to the BEACH!
Full size kitchen with a dish washer & dryer and granite counter tops

NEW: Free standing Cottage within steps to the BEACH!

9.8 out of 10, Exceptional, (6)
"Me and wife came down for the weekend. It was perfect place for us. It was very clean. It was close to beach and the town with night life and restaurants."
NEW: Free standing Cottage within steps to the BEACH!
Cozy Beach Cottage
Exterior

Cozy Beach Cottage

9.2 out of 10, Wonderful, (17)
"Great fun Surf and bay fishing "
Cozy Beach Cottage
Villa Margarita Sparkles
Our interior designer worked her magic to blend modern amenities, upscale coastal accents and nostalgic beach cottage charm! Fully equipped kitchenette makes dining in a breeze or walk just 8 minutes down beach to 5 popular Key restaurants

Villa Margarita Sparkles

9.8 out of 10, Exceptional, (135)
"We loved this property/location. Unfortunately we had to leave a day early due to Helene. The owner was very concerned about this and offered to refund us the day we missed. I would definitely stay here again. "
Villa Margarita Sparkles
Island-Life-Steps to Stunning Beach! Pool!
Free shared use of our kayaks to explore a natural wonderland of Lemon Bay's glorious waters - dolphins often spotted and sometimes manatee

Island-Life-Steps to Stunning Beach! Pool!

10.0 out of 10, Exceptional, (2)
"So cute and cozy! Perfect location for a beach getaway. Teeny Martini looked just like the pictures! Great communication, accommodations at an awesome price. I would recommend a stay at this property."
Island-Life-Steps to Stunning Beach! Pool!
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Exterior detail

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (110)
"Great family house. Management is excellent."
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Beach Road Ariel View

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (170)
"It was a quiet place we ended up not going very many places."
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Beachside Vacation Cottage at Beach Palms

Beachside Vacation Cottage at Beach Palms

10.0 out of 10, Exceptional, (2)
"Great location and very clean and comfortable. Nice to see the old cottages not only saved but remodeled on the inside. Owner's are some of the nicest people you've ever met. Planning the next trip as we speak and will definitely be staying here!"
Beachside Vacation Cottage at Beach Palms
5 Min walk to Bch & Village, Bicycle's Private Pool, On the Canal 502-639-4259
Pool

5 Min walk to Bch & Village, Bicycle's Private Pool, On the Canal 502-639-4259

9.8 out of 10, Exceptional, (13)
"Jim was a fantastic host for me and my new wife. The property was as advertised and a perfect location for privacy and accessibility to the neighborhood. We will hopefully be going back at some point in the near future for a return trip , 10/10!"
5 Min walk to Bch & Village, Bicycle's Private Pool, On the Canal 502-639-4259
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Living space.

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

10.0 out of 10, Exceptional, (1)
"Great Vacation! Very clean and everything you needed. Name “solitude” is appropriate. Nice quiet getaway from hustle and bustle of spring break crowd. Lisa the property manager was very nice and accommodating."
The price is AED 441
AED 1,117 total
includes taxes & fees
9 Dec - 10 Dec
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Villa Mojito Dazzles
Only 1 minute walk to Breathtaking Manasota Key beaches which never get crowded. Our beach is one of best places to find pre-historic sharks teeth area is famous for! The ultimate unique free souvenirs!

Villa Mojito Dazzles

9.6 out of 10, Exceptional, (135)
"The property was very clean, neat, and well equipped. Elena was very kind and helpful and easy to find. Of course the location is excellent. Exceeded our expectations. "
Villa Mojito Dazzles
Beachy Cottage near Manasota Key
Beach

Beachy Cottage near Manasota Key

9.6 out of 10, Exceptional, (4)
"My husband and I spent 40 nights at this cottage. We had an overall good experience. This quaint old place was clean with the exception of a few ants. The appliances, including air conditioning (and heat) all worked. The unit had some broken blinds in the smaller bedroom. I mentioned this via text to our host Allen when we first arrived. He responded that the property manager Olivia was probably aware. We purchased a shower curtain and tacked it up so our guests had privacy. The road is very...
Beachy Cottage near Manasota Key
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Your own privet spa!! cleaned and sanitized after every guest!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

9.6 out of 10, Exceptional, (7)
"Our family stayed at La Mia Casa, the listing of the rental was accurate so we weren’t surprised by anything. The host does a WONDERFUL job of providing any and everything you might need while you stay. The proximity to the beach and points of interest is great it never took us more than 10-15mins to go to the beach or eateries. Our host even extended our checkout which I thought was very nice."
The price is AED 459
AED 1,200 total
includes taxes & fees
26 Nov - 27 Nov
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Waterfront Nokomis Escape w/ Dock, Kayaks & Bikes!
Terrace/patio

Waterfront Nokomis Escape w/ Dock, Kayaks & Bikes!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was very nice, great location. In the waterway, dock had amazing views. Would def come back. Dave was an exceptional host."
Waterfront Nokomis Escape w/ Dock, Kayaks & Bikes!
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 property types in Osprey

Hibiscus Suites - Gateway to Siesta Key
Outdoor pool

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2074)
"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 AED 643
AED 705 total
includes taxes & fees
24 Nov - 25 Nov
Hibiscus Suites - Gateway to Siesta Key
The Residences at Siesta Key Beach by Hyatt Vacation Club
Exterior

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (211)
"This property is off the charts wonderful. Beautiful grounds, kind staff and incredible rooms. Loved every minute of our four night stay!"
The price is AED 1,363
AED 1,700 total
includes taxes & fees
4 Dec - 5 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club
Tropical Beach Resorts
Outdoor pool

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. "
Tropical Beach Resorts
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

How much do cottages in Osprey cost?
You can expect to pay between AED 441 and AED 1,462 per night for cottages in Osprey. Whatever your budget, an ideal stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Osprey?
Osprey has multiple cottages with a total average guest review rating of 9.7. The Inn On Siesta Key is a fantastic option if you like a natural setting and an easy-breezy pace. Guests staying at this 3.5-star stay can enjoy conveniences such as individually decorated rooms and pool sun loungers. Flip Flop Cottages is another popular pick. This 3-star cottage has a swimming pool and individually decorated rooms.
How many cottages are there in Osprey?
Enjoy reconnecting with nature in one of the 253 cottages available in Osprey. To help you reserve an ideal place, take advantage of our filters to search for perks or amenities you need.
Why book your cottage in Osprey with Expedia?
Expedia has some terrific cottages in Osprey, so start packing for a memorable vacation on nature’s doorstep. If you have a fixed budget, choose how much you’re willing to spend and your preferred property star rating. Or take advantage of our filters to search for cottages with a pool or a kitchen. We’ll help you find the perfect digs whatever your escape looks like.
How can I find cheap cottages in Osprey?
Expedia can help you track down cheap cottages in Osprey. To find your ideal stay in a couple of clicks, simply use our handy filter tool to tailor your search results by star rating, budget and amenities.