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Compare 248 Cottages in Osprey with updated reviews, rates, and availability.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (171)
"Wonderful stay on maybe the coldest weekend in Florida history. We were worried about if there was even heat... When we walked into our room we were pleased to feel they turned the heat on for us! Great communication and awesome location. "
The price is SAR 1,663
SAR 2,019 total
includes taxes & fees
16 Mar - 17 Mar
The Inn On Siesta Key

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

9.2 out of 10, Wonderful, (51)
"We used this property as an extension to our home a few blocks away. We had a ball and enjoyed visiting and watching the sunsets together as well as beach time. I will use this property again in the future. Location cannot be beat! All the essentials were available. "
The price is SAR 1,868
SAR 3,159 total
includes taxes & fees
2 Apr - 3 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

9.4 out of 10, Exceptional, (181)
"We were actually at a property in Venice Beach, a house with private pool. It was very nicely decorated and so comfortable. Close to everything. We had a blast."
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

Charming cottage for 2 across warm mineral springs park

10.0 out of 10, Exceptional, (2)
"Had everything we needed. Great location. Very friendly. Was perfect for 2 people."
The price is SAR 244
SAR 605 total
includes taxes & fees
31 Mar - 1 Apr
Charming cottage for 2 across warm mineral springs park

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (317)
"Cute beach cottage across street from beach access. It is a little noisy as is right on beach drive but traffic died down by 10-11 pm. Place is equipped well. Only thing it didn't have that we would have used is a toaster. "
Across The Street From #1 Beach

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

10.0 out of 10, Exceptional, (65)
"Wife and I stayed in Flamingo for a month; love the neighborhood and area. Fortunately Lido hasn't gone high rise like surrounding key islands. Flamingo a very comfortable ranch style one story house exactly as advertised. Owners a delight to work with; any issue that came up they were right on it. Booked again for next year!"
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

Villa Margarita Sparkles

9.8 out of 10, Exceptional, (136)
"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! King Bed Studio-Steps to beach

9.4 out of 10, Exceptional, (153)
"Location of this property is superb. The pictures make it look a little bigger than it is but it is a lovely place to stay. Walkable to a couple great restaurants/bars. Easy 3 minute walk to one of the best beaches in Florida. I have to say, the only criticism I have is the parking spot is a little small. Other wise an amazing 5 star stay. Would go again in a heartbeat "
Island Life! King Bed Studio-Steps to beach

Cozy and Kayaks, Shells and Shark Teeth on the Key, 3 minutes walk to beach!

10.0 out of 10, Exceptional, (60)
"Impeccable cleanliness, wonderful location and attention to detail ….with more than everything you could possibly need available! Many thanks for a spectacular vacation! We will be back! "
Cozy and Kayaks, Shells and Shark Teeth on the Key, 3 minutes walk to beach!

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (82)
"Beautiful sunsets and loved walking out to the back patio and onto the beach. Great place for 2 people. "
The price is SAR 1,680
SAR 2,884 total
includes taxes & fees
3 Apr - 4 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (171)
"It was a quiet place we ended up not going very many places."
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Country Cottage Home

9.6 out of 10, Exceptional, (124)
"The house was as described, very quiet area. It was clean, the beds were comfortable, I would highly recommend to friends and families looking for a place in the area."
Country Cottage Home

Cozy Costal Cottage - Minutes to Attractions!

8.6 out of 10, Excellent, (4)
"Everything was exactly as announced as described. Three bedrooms, with very comfortable queen size beds. Close to everything in the Sarasota area. Sunning in backyard every morning with coffee was excellent. Thanks to our host. We did not need anything. "
Cozy Costal Cottage - Minutes to Attractions!

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

9.8 out of 10, Exceptional, (30)
"We were in town for an event at the Ringling museum. The place was very convenient and comfortable. Good directions from owner and when we had an issue with missing coffee maker, she corrected right away."
The price is SAR 844
SAR 1,274 total
includes taxes & fees
23 Mar - 24 Mar
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Sarasota Home in Historic District w/ Patio!

9.6 out of 10, Exceptional, (10)
"This beautiful historic house was everything we hoped for. The location makes it perfect to walk to just about anything in downtown Sarasota. The second bedroom is actually a separate cottage which was perfect when our friend came to visit for a few days. It also provided a quiet place to work. Everything is updated and pristine. Attentive owner. We can't wait to stay here next year!"
Sarasota Home in Historic District w/ Patio!

Pool, Lake & Sunset Views: Home in Sarasota

3.0 star property
10.0 out of 10, Exceptional, (1)
"I’m a photographer. The pond outside the house had lots of birds! So fun! The pool was really nice too. "
Pool, Lake & Sunset Views: Home in Sarasota

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, (112)
"We enjoyed our stay. It is perfect for families and the location is perfect!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (15)
"The house had just been completely renovated due to the recent hurricane damage. Jim did an excellent job with everything to make sure our stay was top-notch. All the furnishings and appliances were brand new. We took the bikes out every day to Siesta Key Beach, which was just down the street. Absolutely amazing, and it took under 5 minutes! The rental location is very close (less than 1 mile) to fun restaurants in Siesta Key Village, with lot's of great bars and shopping. This place has it...
ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal

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

10.0 out of 10, Exceptional, (2)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is SAR 1,500
SAR 2,329 total
includes taxes & fees
23 Mar - 24 Mar
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Villa Mojito Dazzles

9.8 out of 10, Exceptional, (136)
"Amy was a wonderful host. She found a lovely place for us when Manasota Key was devastated by the hurricane. She and her team were great to work with and our stay was wonderful!"
Villa Mojito Dazzles
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

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4582)
"We loved that it was so close to restaurants and grocery also so close to the Beach. One thing that did bother us a bit was the room was very noisy, what i mean is that you could hear people walking by your room talking as if they were in your room. But we will be going back next year!"
The price is SAR 960
SAR 1,169 total
includes taxes & fees
16 Mar - 17 Mar
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2101)
"What I liked about the property was that is was in close proximity to the beach and Siesta Key Village. People at the Resort were very friendly. What I was disappointed in, was that they were having trouble with the cable from a prior storm and had no TV service "
The price is SAR 1,059
SAR 1,196 total
includes taxes & fees
17 Mar - 18 Mar
Hibiscus Suites - Gateway to Siesta Key

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (235)
"❤️"
The price is SAR 338
SAR 593 total
includes taxes & fees
1 Apr - 2 Apr
Tiny House Siesta
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?
Cottages in Osprey range between SAR 244 and SAR 1,868 per night. These stays offer a chance to soak in nature’s beauty — at a price you can afford. 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?
Choose from multiple cottages in Osprey with a total average guest review rating of 9.5. The Inn On Siesta Key is a wonderful place to relax and put your feet up between adventures. This 3.5-star cottage also offers a garden and individually decorated rooms. Flip Flop Cottages is another quality option with visitors in this area. It has a 3-star rating and amenities including a swimming pool and a furnished patio.
How many cottages are there in Osprey?
Take your pick of 248 cottages in Osprey. Whether you’re vacationing with the kids or organizing a weekend break with close friends, Expedia can help you find the right space to get in touch with nature.
Why book your cottage in Osprey with Expedia?
We think that traveling should be simple, so if you’re after cottages in Osprey at a competitive rate, Expedia has you covered. Keep the budget in check and stay in an economical option far away from the city rush, or book a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Osprey?
The quickest way to track down cheap cottages in Osprey is with Expedia’s useful filter tool. Refine your search by budget, amenities and star rating to grab unbeatable deals in just a few keystrokes.