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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Cottages in Osprey and around

Outdoor dining
Charming cottage for 2 across warm mineral springs park
Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (9)
"I'm currently working in the area and this place made it even easier being away from home I've enjoyed the area and the place "
United States
Andy B.
The price is €133
includes taxes & fees
21 Oct - 22 Oct
Charming cottage for 2 across warm mineral springs park
Property grounds
#3 Small house walking distance to Warm Mineral Spring
#3 Small house walking distance to Warm Mineral Spring
9.0 out of 10, Wonderful, (8)
"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 €133
includes taxes & fees
21 Oct - 22 Oct
#3 Small house walking distance to Warm Mineral Spring
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.2 out of 10, Wonderful, (5)
"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 €246
includes taxes & fees
21 Oct - 22 Oct
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
9.2 out of 10, Wonderful, (65)
"We so enjoy this little property loved the beach and it’s coziness would definitely refer ones to it and would stay again found lots of shells and sharks teeth"
United States
Bobbie H.
The price is €388
includes taxes & fees
21 Oct - 22 Oct
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
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.
9.6 out of 10, Exceptional, (79)
"We loved our stay at the Drift Inn. Very clean, just the right amount of room for 4, easy access to the beach and pool. The beds were very comfortable. The owner was very quick to respond to questions from beginning to end. We would stay here again."
United States
Kimberly P.
The price is €262
includes taxes & fees
23 Oct - 24 Oct
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
10.0 out of 10, Exceptional, (1)
"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 €444
includes taxes & fees
21 Oct - 22 Oct
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
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
2.0 star property
The price is €156
includes taxes & fees
20 Nov - 21 Nov
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet 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
8.0 out of 10, Very good, (1)
"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 €494
includes taxes & fees
21 Oct - 22 Oct
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Exterior
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
9.2 out of 10, Wonderful, (175)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
United States
Kim C.
The price is €343
includes taxes & fees
27 Oct - 28 Oct
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Terrace/patio
5 star Guest House heated pool on the water!
5 star Guest House heated pool on the water!
The price is €448
includes taxes & fees
21 Oct - 22 Oct
5 star Guest House heated pool on the water!
Outdoor dining
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
9.4 out of 10, Exceptional, (102)
"Perfect location, right on the water. Very comfortable cottage right on the beach, near restaurants, close to shopping. The bed is very comfortable, nice kitchen and the bathroom shower is amazing. Very nice patio with an amazing view. Will stay here again. "
United States
Roxanne H.
The price is €399
includes taxes & fees
21 Oct - 22 Oct
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
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

Carlisle Inn

Carlisle Inn

10/10 Excellent
"Everything about this hotel was amazing. The staff, grounds, cleanliness, rooms, breakfast, etc. We were here 3 nights and couldn't think of one complaint."
CHRISTOPHER 3-night trip
Posted 2 days ago
Carlisle Inn

Find out more about Osprey

Osprey Cottages information

Number of reviews
297
Accommodation
319 Cottages
Lowest Price
€156
Highest Price
€494

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between €156 and €494 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 9.3. 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 319 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?
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 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.