Search Cottages in Osprey

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 237 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, (166)
"Great place to stay! "
The Inn On Siesta Key
NEW REMODEL 5 Min walk to Bch & Village, Private Pool, On the Canal 502-639-4259
Pool

NEW REMODEL 5 Min walk to Bch & Village, Private Pool, On the Canal 502-639-4259

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...
NEW REMODEL 5 Min walk to Bch & Village, Private Pool, On the Canal 502-639-4259
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 2,678 total
includes taxes & fees
12 Jan - 13 Jan
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Beach

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

9.2 out of 10, Wonderful, (78)
"Love the cottage- was relieved to see that it weathered the storms. Sad to see the destruction of the foliage surrounding. "
The price is AED 1,462
AED 2,588 total
includes taxes & fees
12 Jan - 13 Jan
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Country Cottage Home
Welcome to the Country Cottage

Country Cottage Home

9.6 out of 10, Exceptional, (122)
"Quiet cottage 15 minutes from the venue. Linda was accommodating with our very late arrival. Will stay here again when visiting Bradenton."
Country Cottage Home
Pool, Lake & Sunset Views: Home in Sarasota
Pool

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

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (316)
"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
Siesta Key Old Florida Cottage, Great Location at a Great Price
Old Florida at its Best!

Siesta Key Old Florida Cottage, Great Location at a Great Price

9.0 out of 10, Wonderful, (164)
"We love this cottage ! Even in a hurricane 😉"
Siesta Key Old Florida Cottage, Great Location at a Great Price
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
New screened Florida Room-for relaxing alone or together outside sans bugs!

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

10.0 out of 10, Exceptional, (62)
"Flamingo Cottage offers everything a Florida getaway has to offer. Gracious owners; a lovely, well appointed vintage beach house and a perfect quiet location for an stress-free vacation. We look forward to our return next year!"
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Outdoor dining

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

9.6 out of 10, Exceptional, (66)
"Everything was wonderful and as described in the listing. The master BR sheets were loose and made it hard for me to sleep but maybe it is just different from what I am used to. I would stay here again! Everything was new and fresh!"
The price is AED 422
AED 1,040 total
includes taxes & fees
15 Jan - 16 Jan
Drift Inn A, 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, (104)
"The place was great!!! Kathy and Jerry are excellent hosts!!! They even invited us for thanksgiving dinner with their family and friends! Very relaxing time!!!"
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
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, (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
Cozy Cottage - Minutes from Beaches and Historic Dearborn St!
Living area

Cozy Cottage - Minutes from Beaches and Historic Dearborn St!

10.0 out of 10, Exceptional, (5)
"This was our first booking with VRBO. Could not have asked for better hosts. Jeff and Lexie went above and beyond to make sure we were comfortable. They were very responsive with any questions we had. Beautiful little cottage with all the amenities you need. Thank you Jeff and Lexie. Looking forward to next time!"
Cozy Cottage - Minutes from Beaches and Historic Dearborn St!
Bradenton Cottage w/ Screened Pool: 12 Mi to Beach
Bradenton Vacation Rental | 3BR | 2BA | Step-Free Access | 1,646 Sq Ft

Bradenton Cottage w/ Screened Pool: 12 Mi to Beach

8.8 out of 10, Excellent, (10)
"Was down for National Soccer showcase at Lakewood Ranch. Good location close by and spacious "
Bradenton Cottage w/ Screened Pool: 12 Mi to Beach
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!
Sunlit Sarasota Cottage w/ Screened Porch!
Sarasota Vacation Rental | 1BR | 1BA | 410 Sq Ft | 2 Steps Required

Sunlit Sarasota Cottage w/ Screened Porch!

10.0 out of 10, Exceptional, (1)
"We had the most wonderful stay! Immaculate and welcoming home and the host is exceptional. We had a fantastic stay! I highly recommend for a relaxing stay but also plenty to do! "
Sunlit Sarasota Cottage w/ Screened Porch!
Inviting Sarasota Cottage: 5 Mi to Beach Access!
Sarasota Vacation Rental | 1BR | 1BA | Stairs Required | 800 Sq Ft

Inviting Sarasota Cottage: 5 Mi to Beach Access!

10.0 out of 10, Exceptional, (1)
Inviting Sarasota Cottage: 5 Mi to Beach Access!
Dog-Friendly, Cozy Cottage, Private Patio, Walk to Bay, Near Downtown
23-00000068

Dog-Friendly, Cozy Cottage, Private Patio, Walk to Bay, Near Downtown

Dog-Friendly, Cozy Cottage, Private Patio, Walk to Bay, Near Downtown
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Unassuming exterior belies the roomy interior with 4 bedrooms 3 baths and a pool

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, (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
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.
Don't see what you're looking for?
See all available properties in Osprey
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Osprey

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. "
The price is AED 534
AED 686 total
includes taxes & fees
13 Jan - 14 Jan
Tropical Beach Resorts
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, (220)
"Very lovely (and large!) accommodation. Extremely clean. Front desk staff kind of rude/pretentious.Great location right on the beach at Siesta Key. Heated pool with good poolside bar. Also had a hot tub, which was nice as the weather was a bit cool when we were there. Feel like I was misled a bit based on room description--thought we were booking a room with beach view, but instead got "city view"--which essentially looked into a back alley and at a 7-eleven. For the price/my personal budget,...
The price is AED 1,875
AED 2,305 total
includes taxes & fees
28 Jan - 29 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2085)
"The room was so neat and would definitely recommend anyone needing a one nights stay!! We had a great time! "
The price is AED 547
AED 618 total
includes taxes & fees
16 Jan - 17 Jan
Hibiscus Suites - Gateway to Siesta Key
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 1,462 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 9.6. 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 237 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.