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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Osprey cottages

Exterior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (22 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
$135 nightly
The price is $150
May 2 - May 3
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
Outdoor dining

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Englewood Central
9.8 out of 10, Exceptional, (6 reviews)
"We all had a wonderful stay!!! The home was clean, beautifully furnished and appointed with all sorts of amenities: coffee, tea, beach chairs, towels, laundry detergent and more. The fenced in yard was wonderful for privacy and the dogs. The owners were very responsive to our questions and needs. We would definitely stay here again!!! Not only was the home super cute, it was close to everything: grocery store, pharmacy, downtown, beaches and restaurants. "
United States
Jade C.
$217 nightly
The price is $242
Apr 30 - May 1
Total with taxes and fees
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Exterior

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Manasota Key
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful decor, perfect location to the beach (5min walking). very thoughtful touches throughout the rental. The kitchen is well- equipped with all you need. Bedroom with excellent mattress. The patio with BBQ, kayaks, free parking, beach chair /loungers available, the property was immaculate.10/10. I would recommend""
United States
Anabel P.
$508 nightly
The price is $562
May 1 - May 2
Total with taxes and fees
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Interior

2 Mi to Englewood Beach! Home w/ Private Dock

2 Mi to Englewood Beach! Home w/ Private Dock
3.0 star property
Englewood
$370 nightly
The price is $411
Apr 30 - May 1
Total with taxes and fees
2 Mi to Englewood Beach! Home w/ Private Dock
Exterior

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.8 out of 10, Excellent, (6 reviews)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
$286 nightly
The price is $320
May 24 - May 25
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
$543 nightly
The price is $605
May 3 - May 4
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
Outdoor dining

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
$321 nightly
The price is $321
Apr 30 - May 1
Total with taxes and fees
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Manasota Key
10.0 out of 10, Exceptional, (6 reviews)
"This was a great stay. It was very clean and seemed like a brand new renovation. They provide plenty to do from two bicycles for cruising, a few kayaks and indoor games. The kitchen was stocked if you chose to stay in and cook. Lastly, the hosts were great to work with. We will stay again. "
United States
John C.
$457 nightly
The price is $506
Apr 30 - May 1
Total with taxes and fees
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Exterior

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

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
$270 nightly
The price is $301
May 20 - May 21
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (182 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
$449 nightly
The price is $501
May 10 - May 11
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Outdoor dining

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Nokomis
9.6 out of 10, Exceptional, (4 reviews)
"The property was very well stocked, had a bowl for our dog an very clean! It was the petfect place for our visit with local family. The "Florida Room" was lovely and the view was excellent. Very peaceful location."
United States
Marie W.
$180 nightly
The price is $200
May 26 - May 27
Total with taxes and fees
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Fridge, microwave, stovetop, dishwasher

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
$450 nightly
The price is $502
May 20 - May 21
Total with taxes and fees
Lido Key Getaway - Bikes & Beach Gear
Outdoor dining

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
Englewood
10.0 out of 10, Exceptional, (39 reviews)
"Very private beach. Beautiful lodging and everything you need to have a great beach vacation. The host was wonderful and answered questions quickly. The whole package for a memorable vacation. "
United States
Anonymous traveler
$896 nightly
The price is $999
May 16 - May 17
Total with taxes and fees
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
House (3 Bedrooms) | Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
$480 nightly
The price is $538
May 17 - May 18
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota Retreat
Terrace/patio

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (120 reviews)
"Excellent Host, Great location, Excited to return"
United States
Anonymous traveler
$508 nightly
The price is $568
May 4 - May 5
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
Pool

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
$1,216 nightly
The price is $1,322
May 6 - May 7
Total with taxes and fees
Cabana Cottage Across street from Beach and Heated Pool
Terrace/patio

Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
$789 nightly
The price is $867
May 11 - May 12
Total with taxes and fees
Nook Cottage Across street from beach and Heated Pool
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$751 nightly
The price is $848
May 10 - May 11
Total with taxes and fees
Siesta Heron 6 / Sunset
Property grounds

Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
$709 nightly
The price is $790
May 10 - May 11
Total with taxes and fees
Nest Cottage Across street from beach and Heated Pool
Dining

Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
United States
Keeley L.
$777 nightly
The price is $867
May 2 - May 3
Total with taxes and fees
Lookout Cottage Across street from Beach and Heated Pool
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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Top Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Place was lovely Check in was rather poorly done - as in customer experience"
Robert 1-night trip
Posted 1 hour ago
Kompose Boutique Hotel

Find out more about Osprey

Osprey Cottages information

Number of reviews
525
Accommodation
356 Cottages
Lowest Price
$150
Highest Price
$1,322

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between $150 and $1,322 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?
Osprey has multiple cottages with a total average guest review rating of 9.5. The Inn On Siesta Key is a terrific option if you're into nature and an easy-breezy pace. Guests of this 3.5-star stay will have access to a swimming pool and a garden. Flip Flop Cottages is another popular choice. This 3-star cottage features a swimming pool and a barbecue grill.
How many cottages are there in Osprey?
Take your pick of 356 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.
Are there any family-friendly cottages in Osprey?
Many travelers searching for a family-friendly cottage in Osprey choose The Inn On Siesta Key. With a 3.5-star rating and amenities including a nearby beach and a barbecue grill, you're sure to feel right at home here. Another superb option for traveling families is Flip Flop Cottages. A barbecue grill and a picnic area help make this 3-star cottage a comfortable base for your Osprey getaway. Osprey has tons of family-friendly attractions to check out that'll keep the kids entertained. Siesta Key Beach and Venice Beach promise a fun day out for both young and old.
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.
What is there to do in Osprey near my cottage?
The most useful travel accessory is a well-planned itinerary. Oscar Scherer State Park is a good spot to begin your sightseeing in Osprey.

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