Osprey, FL Cottage Rentals from $139

A marina with docked boats, a wooden bridge, and a building with a red roof.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Osprey cottages

A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

1. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Sarasota

Kandra R.

$337 nightly

Oct 25 - Oct 26

Total with taxes and fees

A small house with a porch, surrounded by a grassy yard and dense foliage.

2. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

Nokomis

$226 nightly

Oct 22 - Oct 23

Total with taxes and fees

A residential house with a white fence, a palm tree, and a parked car.

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

South Village

Clarissa S.

$272 nightly

Oct 24 - Oct 25

Total with taxes and fees

A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

4. Direct Beachfront 2BR Cottage on Casey Key!

Casey Key

Dominic C.

$449 nightly

Oct 22 - Oct 23

Total with taxes and fees

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

5. The Inn On Siesta Key

Siesta Key

Stephen

$294 nightly

Oct 19 - Oct 20

Total with taxes and fees

A riverfront restaurant with outdoor seating and a view of the water.

6. NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

Nokomis

Susan C.

$278 nightly

Oct 19 - Oct 20

Total with taxes and fees

A wooden deck with a glass door leading to a lake view, surrounded by greenery.

7. Siesta Heron 6 / Sunset

Siesta Key

$619 nightly

Oct 26 - Oct 27

Total with taxes and fees

A patio area with a grill, potted plants, and a building with a teal door.

8. Beach Tree Cottage,Walk To Beach& Siesta

Siesta Key Village

$325 nightly

Oct 19 - Oct 20

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Osprey Hotel Reviews

Tropical Beach Resorts

10/10 Excellent

"The room was clean. It was great to have the sitting area as well as the kitchen. We loved the pool!! Also, great location close to the beach. The staff was very nice and helpful. All around a great place!"

Cottages at Siesta Key Inn

10/10 Excellent

"The Cottages were sold to Azul Resorts which has another similar location around the corner. The entire complex went through a renovation in December of 2025. Expedia still shows it under the old name, and that was a little confusing when I arrived. It looked very clean and new for the most part. I booked the Studio unit with a King size bed. The bed was comfortable and the pillows were great. There is a 65" TV on the wall. It was exactly the same as the one I have at home which was great because I didn't have to learn how to work it. :-) The location is about 250 ft. from the beach access entrance (#13), which is another 200 foot walking path to the sand. The path leaves you about 150 feet from the water (low tide), and about 100 feet from the water (high tide). So if walking is difficult for you, know that you will walk approximately 550 feet before you can wet your toes in the Gulf of America. Regarding the location, it is about 4 miles South of the Sarasota Village downtown, 3 miles South of the main Sarasota Beach public parking area, but there are plenty of restaurant and tiki bars within 1 or 2 miles of the Azul Resort. The only cons I found were that the pool wasn't heated, and someone operates a chair and umbrella rental service that blocks a huge part of the beach area. There is room to the left of the path, or you can go to the right of the blocked off area. They also leave a small strip in front of the blocked area. We didn't have a problem finding room on d'sand."

Siesta Key Beach Resort and Suites

8/10 Good

"I had a three night stay at this hotel on Siesta Key. Great location, and I walked every where safely alone. Very friendly staff! My comments on the room. - the mattress needs to be replaced in room 102 - a threshold at the door would be nice to keep any critters from crawling into the room. - the dehumidifier in the room makes some very loud sounds, frequently, which woke me often."

Find out more about Osprey

Osprey Cottages information

Number of reviews	496
Accommodation	396 Cottages
Lowest Price	$139
Highest Price	$727

Frequently asked questions

How much do cottages in Osprey cost?

Cottages in Osprey range between $139 and $727 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 396 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

Things to do in Siesta Key

Room 1

Check prices for these dates

Our top choices for Osprey cottages

1. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

2. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

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