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Compare 257 Cottages in Osprey with updated reviews, rates, and availability.

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
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, (48)
"The location of this bungalow was great. Even better that the one next to it was vacant at the time. We spent everyday at the beach in front. The beach is amazing. There were plenty of beach towels available. We had to take the beach chairs, umbrella, and noodles from next door which we assumed was the sister property. Other than that the bungalow was comfortable and had good parking right in front. The back deck was a plus to watch the sunset and turtle that would come over once per day to...
The price is AED 911
AED 1,989 total
includes taxes & fees
6 Oct - 7 Oct
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Siesta Beach Cottage, Sleeps 6, Easy Walk to the Beach, Stores, & Restaurants. Amazing Location!
Siesta Beach Cottage, Sleeps 6, Easy Walk to the Beach, Stores, & Restaurants. Amazing Location!
7.4 out of 10, Good, (22)
"10 out of 10 recommend!!! This place was so cute and very clean. We had 5 girls and we all slept very comfortable. The location is AMAZING, you are so close to everything. The management was super fast to get back to us if we had any question. We will be back, hopefully soon😊"
Siesta Beach Cottage, Sleeps 6, Easy Walk to the Beach, Stores, & Restaurants. Amazing Location!
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, (134)
"4 day stay, perfect location, one block from the gulf... Had everything I needed. Quiet, convenient to beach, supplies within a couple of miles, groceries the same. Loved it. Would stay there again."
Villa Mojito Dazzles
Manasota Key Inn 1 BR Suite w/Full Kitchen, Steps to Private Beach, Dog Friendly
PARADISE
Manasota Key Inn 1 BR Suite w/Full Kitchen, Steps to Private Beach, Dog Friendly
9.2 out of 10, Wonderful, (56)
"Cottage was very comfortable. Had everything we needed. Steps from the beautiful Manasota Key beach."
Manasota Key Inn 1 BR Suite w/Full Kitchen, Steps to Private Beach, Dog Friendly
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!
Mermaid Cottage
Exterior detail
Mermaid Cottage
10.0 out of 10, Exceptional, (3)
"We had a wonderful time at Mermaid Cottage. It was clean and welcoming. We had all the amenities we needed and the location was easy to get to every place!! We will be back!!!"
Mermaid Cottage
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
7.8 out of 10, Good, (27)
"Let me start by saying that overall this house was OK for our stay. It was just the 2 of us, so we really didn't need anything bigger. As previous reviews said, the shower is small. However, I'm 6'2" tall and about 240 lbs and I was able to use it without much issue. There are some things about the house that, to someone with an eye for it, need a little attention. You can definitely tell the house gets the attention it needs just for rental season to keep it OK. The shelf in the bathroom behind...
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
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
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
Manasota Key Inn 1 BR Suite w/Full Kitchen, steps to Private Beach, Dog Friendly
Gorgeous Gulf of Mexico
Manasota Key Inn 1 BR Suite w/Full Kitchen, steps to Private Beach, Dog Friendly
9.2 out of 10, Wonderful, (61)
"We loved the place and location, but we have a few suggestions for future guests that might make their stay more enjoyable....Weather strip the front door...we had about 10 cockroaches crawl in while we were there. Hang hooks on the wall for hats, beachwear, leashes, etc. Print instructions for thermostat. It kept wanting a Pin # which we didn't know. Put a mat or rug inside front door. Other than that, everything was perfect!"
Manasota Key Inn 1 BR Suite w/Full Kitchen, steps to Private Beach, Dog Friendly
Beachside Vacation Cottage at Beach Palms in Siesta Key
Beachside Vacation Cottage at Beach Palms in Siesta Key
10.0 out of 10, Exceptional, (1)
"The pictures were accurate! The cottage was quaint!"
Beachside Vacation Cottage at Beach Palms in Siesta Key
Gorgeous Cottage - Steps From Beach Access - Heated Pool
Beautiful heated pool/spa
Gorgeous Cottage - Steps From Beach Access - Heated Pool
10.0 out of 10, Exceptional, (147)
"This was perfect peaceful bliss after an amazingly crap work week!! If you need to escape from life, pack a backpack of bathing suits, sunscreen, a few cover up dresses, and a cooler of your favorite snacks and beverages ‘cuz everything else is in this VBRO! The pool is perfect and the bed is soft with comfy sheets! The little town is just a 5 min walk away for real meals and shops… but truly the space makes your whole Soul say AHHHH!! Thanks! Stacy & Jay "
Gorgeous Cottage - Steps From Beach Access - Heated Pool
Gorgeous Cottage Steps From Beach Access - Heated Pool
Beautiful heated pool and spa
Gorgeous Cottage Steps From Beach Access - Heated Pool
10.0 out of 10, Exceptional, (120)
"This beautifully updated retro cottage comes with it's own pool and hot tub. Minutes from Siesta Key Village and the beach, the host has thought of everything to make you beach vacation relaxed and stress free. Have coffee on the private screened porch while hearing the call of seabirds and gentle chirping of little frogs. The cozy spaces are immaculate, and cheery. If you love the look and feel of 'old Florida' with a sweet uodated interior, this place will capture a special place in your heart...
Gorgeous Cottage Steps From Beach Access - Heated Pool
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!
9.6 out of 10, Exceptional, (5)
"This property is great. It was clean "
NEW: Free standing Cottage within steps to the BEACH!
Charming Beach Cottage Steps to Siesta Beach and Village Shops and Restaurants
Charming Beach Cottage Steps to Siesta Beach and Village Shops and Restaurants
8.0 out of 10, Very Good, (14)
"A nice small space for short stays. Wish they offered a dresser, had to live a week out of suitcases and there was plenty of room for them to offer a dresser in the closet. Too few places to hang towels to dry outside. Kitchen offering is limited but you can get by. Walking distance to town and beaches."
Charming Beach Cottage Steps to Siesta Beach and Village Shops and Restaurants
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Absolutely breathtaking sunsets on the beach!
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
9.4 out of 10, Exceptional, (180)
"Everything was great only thing it needed to have was a tv in the master bedroom "
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Manasota Key Inn 2BR Suite w/Full Kitchen, Private Beach, Dog Friendly
View to the left on our private beach
Manasota Key Inn 2BR Suite w/Full Kitchen, Private Beach, Dog Friendly
9.6 out of 10, Exceptional, (63)
"As nice as I expected. I loved the location and how close it was to the beach. It did seem to have a smoking smell in the unit. I just washed everything when I got home. I may have missed that it was ok to smoke. I would definitely rent again without the smell. "
Manasota Key Inn 2BR Suite w/Full Kitchen, Private Beach, Dog Friendly
Kayaks and Cozy on the Key! 3min walk to beach Sunsets! Short walk to Stump Pass
Terrace/patio
Kayaks and Cozy on the Key! 3min walk to beach Sunsets! Short walk to Stump Pass
10.0 out of 10, Exceptional, (70)
"Booked a last minute staycation and am really glad I did. Excellent location, close to several beaches and tons of ame ities like bikes, SUPs and kayaks. Don't hesitate to stay here"
Kayaks and Cozy on the Key! 3min walk to beach Sunsets! Short walk to Stump Pass
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)
"Everything was perfect. Location was great, and had a good time."
Villa Margarita Sparkles
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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
Outdoor pool
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4535)
"The people who worked there where so pleasant and even the other customers seem to enjoy there stay "
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2070)
"Very clean. Friendly staff. Spacious suite. Though the furniture is not very comfortable. But all in all, it wasn’t too bad if a stay. "
The price is AED 659
AED 721 total
includes taxes & fees
6 Oct - 7 Oct
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
9.6 out of 10, Exceptional, (208)
"Everyone on the staff was wonderful, fun and friendly! The resort is beautiful and soooo accommodating! "
The price is AED 1,620
AED 1,985 total
includes taxes & fees
23 Oct - 24 Oct
The Residences at Siesta Key Beach by Hyatt Vacation Club
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 AED484 and AED484 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 9.3. The Inn On Siesta Key is a terrific option if you like a natural setting and an unhurried pace. Travelers staying at this 3.5-star stay will have access to pool sun loungers and premium bedding. Flip Flop Cottages also comes highly recommended. This 3-star cottage comes with a barbecue grill and a swimming pool.
How many cottages are there in Osprey?
Enjoy reconnecting with nature in one of the 257 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.