Search Osprey Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Osprey cottages

Exterior

Cottage in Warm Mineral Springs

#3 Small house walking distance to Warm Mineral Spring
9.2 out of 10, Wonderful, (13 reviews)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is ￥9,558
￥24,787 total
includes taxes & fees
Mar 16 - Mar 17
#3 Small house walking distance to Warm Mineral Spring
Exterior

Cottage in Warm Mineral Springs

Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (17 reviews)
"Property was perfect for the price."
United States
William M.
The price is ￥9,558
￥24,787 total
includes taxes & fees
Mar 26 - Mar 27
Charming cottage for 2 across warm mineral springs park
Interior

Cottage in Fruitville

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Family Fun: Ping Pong, Bbq, Walk to Park Nearby
House (3 Bedrooms) | Interior

Cottage in North Port

5 Mi to Golf & Trails: North Port Retreat w/ Pool
3.0 star property
10.0 out of 10, Exceptional, (1 review)
"The house had everything we needed, great location & neighborhood also."
United States
Gina
The price is ￥20,348
￥72,636 total
includes taxes & fees
Mar 15 - Mar 16
5 Mi to Golf & Trails: North Port Retreat w/ Pool
Exterior

Cottage in Manasota Key

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
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 ￥28,615
￥75,130 total
includes taxes & fees
Apr 1 - Apr 2
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Exterior

Cottage in Vamo

Chic cottage, Vamo area, close to beaches, pet friendly, kayaks
9.8 out of 10, Exceptional, (24 reviews)
"Nice place "
United States
Viktoriia
The price is ￥46,595
￥91,650 total
includes taxes & fees
Mar 22 - Mar 23
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks
Exterior

Cottage in Manasota Beach

Cozy Beach Cottage
9.4 out of 10, Exceptional, (24 reviews)
"Wonderful location for a peaceful getaway "
United States
pamela
The price is ￥47,471
￥100,954 total
includes taxes & fees
Mar 28 - Mar 29
Cozy Beach Cottage
Terrace/patio

Cottage in Casey Key

Direct Beachfront 2BR Cottage on 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 ￥63,401
￥112,010 total
includes taxes & fees
Apr 9 - Apr 10
Direct Beachfront 2BR Cottage on Casey Key!
Outdoor dining

Cottage in Englewood Central

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and nicely decorated condo. Appreciated the extras...dish soap, soap, shampoo and body wash, & TP. Also, beach chairs and towels! Nice outside area and short drive to beaches. Host is very responsive...issue with heat resolved same day. "
United States
Susan E.
The price is ￥25,435
￥56,021 total
includes taxes & fees
Mar 28 - Mar 29
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Exterior

Cottage in Sarasota

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
8.8 out of 10, Excellent, (3 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 ￥24,322
￥54,866 total
includes taxes & fees
Mar 17 - Mar 18
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Exterior

Cottage in South Village

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (85 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is ￥15,771
￥46,368 total
includes taxes & fees
Mar 26 - Mar 27
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

Cottage in Manasota Key

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
10.0 out of 10, Exceptional, (5 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 ￥27,025
￥73,349 total
includes taxes & fees
Apr 5 - Apr 6
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Interior

Cottage in Sarasota

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
The price is ￥9,958
￥58,436 total
includes taxes & fees
Mar 18 - Mar 19
Stylish Retro Vibes Private BBQ & Beach Access
House (4 Bedrooms) | Interior

Cottage in Bradenton

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
The price is ￥32,019
￥106,627 total
includes taxes & fees
Mar 24 - Mar 25
Outdoor Kitchen & Gaming Garage: Bradenton Retreat
Exterior

Cottage in Siesta Key Village

Blue Dolphin Cottage steps from the beach
The price is ￥55,504
￥139,148 total
includes taxes & fees
Mar 19 - Mar 20
Blue Dolphin Cottage steps from the beach
Outdoor dining

Cottage in Siesta Key

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.6 out of 10, Exceptional, (7 reviews)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
The price is ￥61,331
￥99,085 total
includes taxes & fees
Mar 21 - Mar 22
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cottage in Indian Beach Sapphire Shores

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
9.6 out of 10, Exceptional, (34 reviews)
"Fun stay, great location"
United States
Theresa H.
The price is ￥26,285
￥41,888 total
includes taxes & fees
Apr 7 - Apr 8
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Terrace/patio

Cottage in Casey Key

Casey Key Beachfront Escape: Charming 1BR Cottage
9.4 out of 10, Exceptional, (113 reviews)
"Excellent Host, Great location, Excited to return"
United States
Anonymous traveler
The price is ￥47,373
￥91,653 total
includes taxes & fees
Mar 14 - Mar 15
Casey Key Beachfront Escape: Charming 1BR Cottage
The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (194 reviews)
"Great place to stay! "
United States
Carlos
The price is ￥102,319
￥125,500 total
includes taxes & fees
Mar 14 - Mar 15
The Inn On Siesta Key
Terrace/patio

Cottage in Siesta Key

Cabana Cottage Across street from Beach and Heated Pool
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 ￥106,280
￥231,367 total
includes taxes & fees
Mar 14 - Mar 15
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

8/10 Good
"I just found it very rude that the hallways smelled like dirty wet carpet. Please do better, other than that. I loved the hotel and my room. "
Chanda 3-night trip
Posted 7 hours ago
Kompose Boutique Hotel

Find out more about Osprey

Osprey Cottages information

Number of reviews
395
Accommodation
325 Cottages
Lowest Price
￥24,787
Highest Price
￥231,367

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between ￥24,787 and ￥231,367 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 9.6. 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 325 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.

Explore a world of travel with Expedia