Search Osprey Cottages

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Cottages in Osprey

Relax in Hot Tub, Walk to Springs: North Port Home

3.0 star property
North Port
$186 nightly
The price is $207
Nov 19 - Nov 20
Total with taxes and fees
Relax in Hot Tub, Walk to Springs: North Port Home

Charming cottage for 2 across warm mineral springs park

Warm Mineral Springs
9.2 out of 10, Wonderful, (10)
"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.
$140 nightly
The price is $156
Nov 18 - Nov 19
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

#3 Small house walking distance to Warm Mineral Spring

Warm Mineral Springs
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.
$140 nightly
The price is $156
Nov 18 - Nov 19
Total with taxes and fees
#3 Small house walking distance to Warm Mineral Spring

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
$219 nightly
The price is $248
Nov 18 - Nov 19
Total with taxes and fees
The Inn On Siesta Key

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

2.0 star property
Nokomis
10.0 out of 10, Exceptional, (1)
"Host was very accommodating and kind. The cottage was cozy and well kept. Waking up with the ocean breeze off the river and the quiet neighborhood was so relaxing. I would highly recommend!"
United States
Michael A.
$153 nightly
The price is $170
Dec 1 - Dec 2
Total with taxes and fees
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Island Life! King Bed Studio-Steps to beach

Manasota Key
9.6 out of 10, Exceptional, (169)
"My husband and I stayed at the Bay Breeze Bungalow for 4 days and cannot wait to come back. Perfect location, 2 minute walk to the beach. Quiet neighborhood. We were right next to the pool, and even with kids swimming, it was quiet. We had a question regarding parking, (our confusion) we received a call back within a 1/2 hour. The Bungalow was very clean and had the essentials we needed. Being May, it was extremely warm, the air conditioner always kept the place cool. I cannot say enough...
United States
Karen L.
$178 nightly
The price is $196
Nov 30 - Dec 1
Total with taxes and fees
Island Life! King Bed Studio-Steps to beach

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

2.0 star property
Englewood Central
$194 nightly
The price is $216
Nov 18 - Nov 19
Total with taxes and fees
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

Manasota Key
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.
$460 nightly
The price is $509
Nov 18 - Nov 19
Total with taxes and fees
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

Manasota Key
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.
$511 nightly
The price is $565
Nov 18 - Nov 19
Total with taxes and fees
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Casey Key
9.2 out of 10, Wonderful, (69)
"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.
$513 nightly
The price is $572
Nov 18 - Nov 19
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Nest Cottage Across street from beach and Heated Pool

Siesta Key
10.0 out of 10, Exceptional, (2)
"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.
$428 nightly
The price is $477
Nov 19 - Nov 20
Total with taxes and fees
Nest Cottage Across street from beach and Heated Pool

5 star Guest House heated pool on the water!

South Sarasota
$457 nightly
The price is $509
Nov 18 - Nov 19
Total with taxes and fees
5 star Guest House heated pool on the water!

Haven cottage Across street from beach and Heated Pool

Siesta Key
9.8 out of 10, Exceptional, (7)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
United States
Michael M.
$422 nightly
The price is $470
Nov 18 - Nov 19
Total with taxes and fees
Haven cottage Across street from beach and Heated Pool

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Casey Key
9.4 out of 10, Exceptional, (106)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
$519 nightly
The price is $579
Nov 18 - Nov 19
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Osprey Hotel Reviews

Find out more about Osprey

Osprey Cottages information

Number of reviews
544
Accommodation
319 Cottages
Lowest Price
$156
Highest Price
$579

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between $156 and $579 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 9.2. 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 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