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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Osprey cottages

Exterior

Cottage in Warm Mineral Springs

Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (18 reviews)
"Property was perfect for the price."
United States
William M.
The price is €139
includes taxes & fees
26 Mar - 27 Mar
Charming cottage for 2 across warm mineral springs park
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 €149
includes taxes & fees
31 Mar - 1 Apr
#3 Small house walking distance to Warm Mineral Spring
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 €396
includes taxes & fees
28 Mar - 29 Mar
5 Mi to Golf & Trails: North Port Retreat w/ Pool
Interior

Cottage in Sarasota

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
The price is €340
includes taxes & fees
23 Mar - 24 Mar
Stylish Retro Vibes Private BBQ & Beach Access
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 €545
includes taxes & fees
28 Mar - 29 Mar
Cozy Beach Cottage
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 €495
includes taxes & fees
22 Mar - 23 Mar
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks
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 €412
includes taxes & fees
1 Apr - 2 Apr
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
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 €300
includes taxes & fees
22 Mar - 23 Mar
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
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 €288
includes taxes & fees
28 Mar - 29 Mar
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Terrace/patio

Cottage in Casey Key

Casey Key Beachfront Escape: Charming 1BR Cottage
9.4 out of 10, Exceptional, (114 reviews)
"Excellent Host, Great location, Excited to return"
United States
Anonymous traveller
The price is €502
includes taxes & fees
22 Mar - 23 Mar
Casey Key Beachfront Escape: Charming 1BR Cottage
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.
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 €402
includes taxes & fees
5 Apr - 6 Apr
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
House (4 Bedrooms) | Interior

Cottage in Bradenton

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
The price is €580
includes taxes & fees
24 Mar - 25 Mar
Outdoor Kitchen & Gaming Garage: Bradenton Retreat
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 €427
includes taxes & fees
22 Mar - 23 Mar
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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 €563
includes taxes & fees
24 Mar - 25 Mar
The Inn On Siesta Key
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 €238
includes taxes & fees
7 Apr - 8 Apr
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Terrace/patio

Cottage in Siesta Key

Nook Cottage Across street from beach and Heated Pool
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 €851
includes taxes & fees
24 Mar - 25 Mar
Nook Cottage Across street from beach and Heated Pool
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 €1,192
includes taxes & fees
23 Mar - 24 Mar
Cabana Cottage Across street from Beach and Heated Pool
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 €630
includes taxes & fees
12 Apr - 13 Apr
Direct Beachfront 2BR Cottage on Casey Key!
House (3 Bedrooms) | Front of property

Cottage in Siesta Key

Siesta Heron 7
3.0 star property
The price is €1,525
includes taxes & fees
23 Mar - 24 Mar
Siesta Heron 7
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
"We loved the location and the property beach access was great. The daily room service was a bonus. "
Brenda 7-night trip
Posted 3 hours ago
Tropical Beach Resorts

Find out more about Osprey

Osprey Cottages information

Number of reviews
383
Accommodation
336 Cottages
Lowest Price
€139
Highest Price
€1,525

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between €139 and €1,525 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 336 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.