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

Search Osprey Cottage Rentals from CA $194

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Osprey cottages

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is CA $112
CA $358 total
includes taxes & fees
Sep 29 - Sep 30
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

2. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 reviews)
"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 $135
CA $804 total
includes taxes & fees
Sep 20 - Sep 21
Yellow Palm Cottage steps from the beach

3. 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, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is CA $138
CA $421 total
includes taxes & fees
Sep 28 - Sep 29
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

4. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is CA $347
CA $720 total
includes taxes & fees
Sep 26 - Sep 27
Casey Key Beachfront Escape: Charming 1BR Cottage

5. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is CA $145
CA $820 total
includes taxes & fees
Sep 30 - Oct 1
Pink Mango Cottage steps from the beach

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
The price is CA $334
CA $645 total
includes taxes & fees
Sep 20 - Sep 21
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

7. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $533
CA $971 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Heron 6 / Sunset

8. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is CA $175
CA $485 total
includes taxes & fees
Oct 4 - Oct 5
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

9. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is CA $131
CA $803 total
includes taxes & fees
Sep 24 - Sep 25
Blue Dolphin Cottage steps from the beach

10. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (83 reviews)
"Great vacation!!"
United States
Dominic C.
The price is CA $277
CA $709 total
includes taxes & fees
Sep 23 - Sep 24
Direct Beachfront 2BR Cottage on Casey Key!

11. 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, (191 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is CA $297
CA $559 total
includes taxes & fees
Sep 21 - Sep 22
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

12. Coastal Studio, Walk to St Armand's or Lido Beach

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
The price is CA $138
CA $486 total
includes taxes & fees
Sep 20 - Sep 21
Coastal Studio, Walk to St Armand's or Lido Beach

13. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is CA $131
CA $451 total
includes taxes & fees
Sep 23 - Sep 24
Cozy Lido Studio by Beach & St Armand's

14. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is CA $131
CA $479 total
includes taxes & fees
Sep 28 - Sep 29
Lido Key Casita w Pool Steps to the Beach

15. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
The price is CA $126
CA $334 total
includes taxes & fees
Sep 20 - Sep 21
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

16. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (29 reviews)
"We were enjoying our stay."
United States
Inna K.
The price is CA $63
CA $194 total
includes taxes & fees
Oct 1 - Oct 2
Charming cottage for 2 across warm mineral springs park

17. Real Florida Up Close! Family-friendly, Pet-friendly with private pool

Real Florida Up Close! Family-friendly, Pet-friendly with private pool
Sarasota
The price is CA $255
CA $437 total
includes taxes & fees
Sep 20 - Sep 21
Real Florida Up Close! Family-friendly, Pet-friendly with private pool

18. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is CA $131
CA $476 total
includes taxes & fees
Sep 20 - Sep 21
Studio by Lido Beach w heated pool

19. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is CA $833
CA $1,175 total
includes taxes & fees
Oct 2 - Oct 3
Beach Road

20. 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 $210
CA $624 total
includes taxes & fees
Sep 20 - Sep 21
Home < 1-mi Walk to Warm Mineral Springs Park!
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
413
Accommodation
389 Cottages
Lowest Price
CA $194
Highest Price
CA $1,175

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between CA $194 and CA $1,175 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 389 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.

Explore a world of travel with Expedia