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

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Osprey cottages

Exterior

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is AED 294
AED 921 total
includes taxes & fees
20 Sep - 21 Sep
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Exterior

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.
Yellow Palm Cottage steps from the beach
Exterior

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 AED 364
AED 1,073 total
includes taxes & fees
23 Sep - 24 Sep
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Property grounds

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 AED 911
AED 1,920 total
includes taxes & fees
26 Sep - 27 Sep
Casey Key Beachfront Escape: Charming 1BR Cottage
Property grounds

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)
Pink Mango Cottage steps from the beach
Exterior

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

7. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is AED 1,399
AED 2,550 total
includes taxes & fees
30 Sep - 1 Oct
Siesta Heron 6 / Sunset
Outdoor dining

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

9. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
Blue Dolphin Cottage steps from the beach
Terrace/patio

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 AED 727
AED 1,788 total
includes taxes & fees
20 Sep - 21 Sep
Direct Beachfront 2BR Cottage on Casey Key!
Exterior

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 AED 807
AED 1,524 total
includes taxes & fees
21 Sep - 22 Sep
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Hair dryer, towels, soap, shampoo

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 AED 364
AED 1,280 total
includes taxes & fees
20 Sep - 21 Sep
Coastal Studio, Walk to St Armand's or Lido Beach
1 bedroom, iron/ironing board, WiFi, bed sheets

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is AED 343
AED 1,206 total
includes taxes & fees
23 Sep - 24 Sep
Cozy Lido Studio by Beach & St Armand's
Pool

14. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is AED 343
AED 1,243 total
includes taxes & fees
24 Sep - 25 Sep
Lido Key Casita w Pool Steps to the Beach
Exterior

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 AED 331
AED 880 total
includes taxes & fees
26 Sep - 27 Sep
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Exterior

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 AED 165
AED 509 total
includes taxes & fees
1 Oct - 2 Oct
Charming cottage for 2 across warm mineral springs park
Outdoor banquet area

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 AED 668
AED 1,132 total
includes taxes & fees
20 Sep - 21 Sep
Real Florida Up Close! Family-friendly, Pet-friendly with private pool
Outdoor dining

18. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
Studio by Lido Beach w heated pool
Interior

19. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is AED 2,172
AED 3,070 total
includes taxes & fees
21 Sep - 22 Sep
Beach Road
House (4 Bedrooms) | Interior

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 AED 551
AED 1,638 total
includes taxes & fees
20 Sep - 21 Sep
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.
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Top Osprey Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"Very clean"
Wallace 1-night trip
Posted 3 hours ago
Carlisle Inn

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between AED 509 and AED 3,070 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 390 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.
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.