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Our top choices for Osprey cottages

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, (24 reviews)
"Easy check in, clean and cozy."
United States
Robert J.
The price is CA $70
CA $201 total
includes taxes & fees
Jun 12 - Jun 13
Charming cottage for 2 across warm mineral springs park

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, (8 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 CA $98
CA $335 total
includes taxes & fees
Jun 14 - Jun 15
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is CA $222
CA $675 total
includes taxes & fees
Jun 28 - Jun 29
Home < 1-mi Walk to Warm Mineral Springs Park!

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
9.4 out of 10, Exceptional, (3 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 CA $237
CA $652 total
includes taxes & fees
Jun 11 - Jun 12
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

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)
"If you are looking for a quaint getaway in a quiet part of Manasota key, this is it. While you are close enough walk or bike to the beach and all the restaurant/bars, it’s just far enough away from all the congestion. The cottage was beautifully decorated, clean & updated. Truly a great host, they were responsive and provided more items to use than any other VRBO we’ve stayed at! "
United States
Brooke T.
The price is CA $287
CA $715 total
includes taxes & fees
Jun 11 - Jun 12
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 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 CA $544
CA $701 total
includes taxes & fees
Jun 16 - Jun 17
The Inn On Siesta Key

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Southgate
9.6 out of 10, Exceptional, (15 reviews)
"Place had everything needed. Host was very communicative and helpful. "
United States
Chris R.
The price is CA $126
CA $604 total
includes taxes & fees
Jun 30 - Jul 1
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

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

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, (5 reviews)
"Lowkey, quiet, clean, amenities to cook, great host and great view. Happy to go back again."
United States
Bryan S.
The price is CA $160
CA $272 total
includes taxes & fees
Jun 28 - Jun 29
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is CA $135
CA $518 total
includes taxes & fees
Jun 18 - Jun 19
Lido Key Getaway - Bikes & Beach Gear

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is CA $387
CA $1,082 total
includes taxes & fees
Jun 16 - Jun 17
Pink Mango Cottage steps from the beach

3 Mi to Beach! Englewood Family Gem + Private Pool

3 Mi to Beach! Englewood Family Gem + Private Pool
3.0 star property
Englewood
The price is CA $272
CA $722 total
includes taxes & fees
Jun 11 - Jun 12
3 Mi to Beach! Englewood Family Gem + Private Pool

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (74 reviews)
"It was perfect. We had a great time."
United States
Karen M.
The price is CA $276
CA $669 total
includes taxes & fees
Jun 11 - Jun 12
Direct Beachfront 2BR Cottage on Casey Key!

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (39 reviews)
"Fun stay, great location"
United States
Theresa H.
The price is CA $188
CA $325 total
includes taxes & fees
Jun 28 - Jun 29
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

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.
The price is CA $403
CA $1,104 total
includes taxes & fees
Jun 17 - Jun 18
Yellow Palm Cottage steps from the beach

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.
The price is CA $686
CA $1,140 total
includes taxes & fees
Jun 19 - Jun 20
Nest Cottage Across street from beach and Heated Pool

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, (184 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is CA $384
CA $624 total
includes taxes & fees
Jun 15 - Jun 16
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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 CA $645
CA $1,635 total
includes taxes & fees
Jun 15 - Jun 16
Cabana Cottage Across street from Beach and Heated Pool

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (124 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is CA $416
CA $810 total
includes taxes & fees
Jun 14 - Jun 15
Casey Key Beachfront Escape: Charming 1BR Cottage
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

Find out more about Osprey

Osprey Cottages information

Number of reviews
776
Accommodation
378 Cottages
Lowest Price
CA $201
Highest Price
CA $1,658

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between CA $201 and CA $1,658 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 9.7. 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 378 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 travellers 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 travelling 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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