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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 294 Cottages in Osprey with updated reviews, rates, and availability.

The Inn On Siesta Key
The Cabana, 2 Bedroom 2 Bath (1 King, 2 Twins) | Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (172)
"We were happy with everything!"
The price is AED 2,060
AED 2,465 total
includes taxes & fees
5 Apr - 6 Apr
The Inn On Siesta Key
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
On the beach, sun loungers, beach towels

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 AED 1,646
AED 2,828 total
includes taxes & fees
3 Apr - 4 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
On the beach, sun loungers, beach towels

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

9.2 out of 10, Wonderful, (52)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is AED 1,829
AED 3,141 total
includes taxes & fees
25 Mar - 26 Mar
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (172)
"The location and cleanliness was top notch. I would recomend to stay there.The description needs to be updated. It says the place has a murphy Bed. It doesn't. It has a blow up.matress.for the 3rd bed. That was a problem since i need 3 actual beds. I had 1 couple and two friends that didnt share a bed. The description made that not be a problem but it was a problem.. Other then the bed situation in the description it was very good. The description of any place is super important. That needs to...
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Villa Margarita Sparkles
Beach nearby

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
Across The Street From #1 Beach
Beach nearby, sun loungers, beach towels

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (318)
"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "
Across The Street From #1 Beach
ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal
Sun loungers

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

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.
Cozy Cottage in south Sarasota Florida, Close to Beaches!
Beach

Cozy Cottage in south Sarasota Florida, Close to Beaches!

10.0 out of 10, Exceptional, (2)
"Every year, we visit the kids’ grandmother who lives down the street in this neighborhood. The location is fantastic with easy access to her house and to route 41. The beds were comfy. The kitchen had all the amenities. Having two full bathrooms for four individuals including a teenager was a luxury for us. Allen was always respnsive and a great communicator. We’ll be back!"
Cozy Cottage in south Sarasota Florida, Close to Beaches!
Charming cottage for 2 across warm mineral springs park
Fridge, microwave, stovetop, coffee/tea maker

Charming cottage for 2 across warm mineral springs park

10.0 out of 10, Exceptional, (3)
"Enjoyed our stay at this cute cottage located in North Port Florida. Near mineral springs...and other attractions. Good communication with the owner. Check in was seamless. Clean & stocked well!!Thank you!!M & J"
Charming cottage for 2 across warm mineral springs park
Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!
Fridge, microwave, oven, stovetop

Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!

9.4 out of 10, Exceptional, (33)
"Easy access to restaurants and stores. Centrally located makes it easy to get around. Very congested. "
Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!
Country Cottage Home
Fridge, microwave, oven, stovetop

Country Cottage Home

9.6 out of 10, Exceptional, (125)
"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 Cottage - Minutes from Beaches and Historic Dearborn St!
Beach

Cozy Cottage - Minutes from Beaches and Historic Dearborn St!

10.0 out of 10, Exceptional, (11)
"We popped in the area and needed a place to stay for a couple of nights. This was a great spot for just my husband and I. Quiet neighborhood to walk to places and we ate at some really great places too. The beaches are a short drive. We don’t find one close enough to walk to."
Cozy Cottage - Minutes from Beaches and Historic Dearborn St!
Island Life! King Bed Studio-Steps to beach
Aerial view

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
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Sun loungers, beach towels

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

9.6 out of 10, Exceptional, (72)
"We loved everything about this rental! There are so many fun restaurants and bars within walking distance! There's also the convenience of the trolley stop right across the street for trips into the Village. The pool was nice and the beach was very close. We'd definitely recommend this location and we hope to be back next year!"
The price is AED 606
AED 1,405 total
includes taxes & fees
20 Apr - 21 Apr
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Cozy and Kayaks, Shells and Shark Teeth on the Key, 3 minutes walk to beach!
Outdoor dining

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

10.0 out of 10, Exceptional, (62)
"Booked last minute and we were quite impressed. Very clean. Nicely organized and stocked with extras. Small, but fit two adults and a 5 yo for our sleeping very well. "
Cozy and Kayaks, Shells and Shark Teeth on the Key, 3 minutes walk to beach!
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Beach

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."
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Cozy Costal Cottage - Minutes to Attractions!
Fridge, microwave, oven, stovetop

Cozy Costal Cottage - Minutes to Attractions!

8.8 out of 10, Excellent, (5)
"My dad's house, Ed Smith Stadium, VFW Post were within a very short distance. They are all places i frequent since travelling to Sarasota the past 40 years. Lido Key I also enjoy and can also get there within a reasonable time,The neighborhood was confusing to me at first. Different types of homes but it was incredibly quiet and The Cottage was comfortable. Good amenities. No dishwasher or gas grill. The dishwasher wasn't a big deal for me as I was travelling alone but could be for larger...
Cozy Costal Cottage - Minutes to Attractions!
Sarasota Home in Historic District w/ Patio!
Fridge, microwave, stovetop, dishwasher

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
Interior

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
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
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4601)
"The room was OK but the bathtub drain was almost clogged. There is a lot of works going on around this property. Basically, it is a standard motel with a pool."
The price is AED 865
AED 1,060 total
includes taxes & fees
31 Mar - 1 Apr
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
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, (2105)
"Great little hotel close to the beach, but not so close as to be over-priced. Easy 15 min walk to a public beach access in one direction and 10 min walk to several restaurants/groceries in the other direction. Very clean and updated room with a full size refrigerator and small kitchen. The pool was the best part. Comfortable chairs and never crowded."
The price is AED 711
AED 804 total
includes taxes & fees
2 Apr - 3 Apr
Hibiscus Suites - Gateway to Siesta Key
The Ringling Beach House
Aerial view

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (295)
"We very much enjoyed our stay. Our room was clean and ready for us early. Nancy, the manager, couldn’t have been nicer. This is a no-frills place—but the location can’t be beat! You walk across the street to the beach, and the lively shopping area with restaurants and fun is so close. It’s a quick walk, or you can take the free trolleys/busses. The outdoor area with a nice pool was so relaxing. We used it often. We would stay again. We had 3 teens with us, and they had a blast. We all felt safe....
The Ringling Beach House
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 AED 1,646 and AED 2,060 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 294 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.