Compare Osprey Cottage Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Cottages in Osprey

The Inn On Siesta Key

The Inn On Siesta Key

3.5 out of 5
515 Beach Road Siesta Key FL
$384 nightly
The price is $434 total per night
$434 total
Jul 12 - Jul 13
Total with taxes and fees
Guests of The Inn On Siesta Key enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. If you decide to drive, there's free parking. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this beach cottage include a terrace, laundry facilities, and barbecue grills.
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

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

Englewood FL
$211 nightly
The price is $236 total per night
$236 total
Jul 7 - Jul 8
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
5 Min walk to Beach & Village, Private Pool,On the Canal

5 Min walk to Beach & Village, Private Pool,On the Canal

Siesta Key FL
At this cottage, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage

Nokomis FL
$460 nightly
The price is $513 total per night
$513 total
Jul 5 - Jul 6
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

Siesta Key FL
Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sarasota FL
At this cottage, guests have access to features like laundry facilities.
1-bedroom cottage just 10 minutes from Siesta Key Beach

1-bedroom cottage just 10 minutes from Siesta Key Beach

Sarasota FL
At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. This cottage also has a garden.
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

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

Englewood FL
$432 nightly
The price is $479 total per night
$479 total
Jul 5 - Jul 6
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Venice FL
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Don't see what you're looking for?
See all available properties in Osprey
View all properties
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.

Hotel Options in Osprey

    Casey Key Resorts - Mainland

    Casey Key Resorts - Mainland

    1650 South Tamiami Trail Osprey FL
    $114 nightly
    The price is $128 total per night from Jul 5 to Jul 6
    $128 total
    Jul 5 - Jul 6
    Total with taxes and fees
    8.8/10 Excellent! (1,185 reviews)
    Kompose Boutique Hotel

    Kompose Boutique Hotel

    965 University Pkwy Sarasota FL
    $94 nightly
    The price is $107 total per night from Jul 9 to Jul 10
    $107 total
    Jul 9 - Jul 10
    Total with taxes and fees
    9.2/10 Wonderful! (5,604 reviews)
    Golden Host Resort - Sarasota

    Golden Host Resort - Sarasota

    4675 N Tamiami Trl Sarasota FL
    $75 nightly
    The price is $85 total per night from Jul 5 to Jul 6
    $85 total
    Jul 5 - Jul 6
    Total with taxes and fees
    8.6/10 Excellent! (2,579 reviews)

Cottages

Book a cottage in Osprey
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Osprey. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Osprey better.

Cottage apartments in Osprey range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Osprey
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Osprey and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Osprey cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Osprey. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Osprey Cottages essential information

Accommodation
370 Cottages
Lowest Price
$85
Highest Price
$513
Popular accommodation
The Inn On Siesta Key, Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly, 5 Min walk to Beach & Village, Private Pool,On the Canal, Casey Key Beachfront Escape: Charming 1BR Cottage, 🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!, Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, 1-bedroom cottage just 10 minutes from Siesta Key Beach, 2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear, Venetian Vacation! Close To Beaches, Restaurants & Shopping!