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Check prices for these dates

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

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
9.2 out of 10, Wonderful, (23 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is £113
includes taxes & fees
14 May - 15 May
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.
The price is £186
includes taxes & fees
4 May - 5 May
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.
The price is £416
includes taxes & fees
10 May - 11 May
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Exterior

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
7.8 out of 10, Good, (7 reviews)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is £256
includes taxes & fees
23 May - 24 May
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is £360
includes taxes & fees
14 May - 15 May
The Inn On Siesta Key
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.
The price is £449
includes taxes & fees
7 May - 8 May
Direct Beachfront 2BR Cottage on Casey Key!
House (4 Bedrooms) | Interior

Outdoor Kitchen & Gaming Garage: Bradenton Retreat

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
Bradenton
The price is £493
includes taxes & fees
21 May - 22 May
Outdoor Kitchen & Gaming Garage: Bradenton Retreat
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.
The price is £295
includes taxes & fees
13 May - 14 May
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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.
The price is £224
includes taxes & fees
20 May - 21 May
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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.
The price is £373
includes taxes & fees
15 May - 16 May
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Exterior

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
Yellow Palm Cottage steps from the beach
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
The price is £366
includes taxes & fees
10 May - 11 May
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.
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is £561
includes taxes & fees
4 May - 5 May
Pink Mango Cottage steps from the beach
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 traveller
The price is £739
includes taxes & fees
16 May - 17 May
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
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 traveller
The price is £422
includes taxes & fees
4 May - 5 May
Casey Key Beachfront Escape: Charming 1BR Cottage
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
The price is £396
includes taxes & fees
17 May - 18 May
Unwind Poolside + Walk to Beach! Sarasota Retreat
Exterior

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
Blue Dolphin Cottage steps from the beach
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.
The price is £653
includes taxes & fees
11 May - 12 May
Nook Cottage Across street from beach and Heated Pool
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.
The price is £955
includes taxes & fees
10 May - 11 May
Cabana 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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"This was exactly what we expected. The apartment was spacious and well kept. It was quiet and felt safe. It’s a 5 min walk to the beach and close to a shared pool. There wasn’t an outside balcony/ patio but they provide everyone with a couple of chairs which proved great for an early morning light breakfast. "
Timothy 5-night trip
Posted 2 hours ago
Tropical Beach Resorts

Find out more about Osprey

Osprey Cottages information

Number of reviews
700
Accommodation
364 Cottages
Lowest Price
£113
Highest Price
£955

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between £113 and £955 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?
A traveller favourite is The Inn On Siesta Key. Base yourself at this 3.5-star stay which offers a barbecue grill and a memory foam mattress. Flip Flop Cottages is another popular option to consider. Spend your break at this 3-star cottage and make the most of amenities including a barbecue grill and a swimming pool. You'll have your pick of multiple cottages in Osprey with a total average guest review rating of 9.4.
How many cottages are there in Osprey?
Take your pick of 364 cottages in Osprey. Whether you're holidaying with the kids or organising 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?
Holidaying with your group in Osprey couldn't be easier at The Inn On Siesta Key. With conveniences such as a nearby beach and an oven, you'll find all the comforts you need at this 3.5-star cottage. Flip Flop Cottages is another family-friendly property where you and the rest of the squad can take time out from the relentless pace of city life. This cottage has a 3-star rating and amenities including a picnic area and a barbecue grill. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to visit in and around Osprey. Manasota Beach and Heritage Oaks Golf and Country Club guarantee fun for all ages.
Why book your cottage in Osprey with Expedia?
We think that travelling 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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