Longboat Key Cottage Rentals
1200 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $318/Night
For 7 Nights US $2,223
2002.09 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Pool
US $488/Night
For 7 Nights US $3,416
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $228/Night
For 7 Nights US $1,595
1168 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $411/Night
For 7 Nights US $2,879
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $743/Night
For 7 Nights US $5,201
US $312/Night
For 7 Nights US $2,184
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $424/Night
For 7 Nights US $2,968
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $593/Night
For 7 Nights US $4,149
1259.38 ft²
4 Guests
2 Bedrooms
1 Bathroom
Apartment
- Private Pool
- Private Beach
- Oceanfront
US $283/Night
For 7 Nights US $1,981
700 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $433/Night
For 7 Nights US $3,032
333.68 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Private Beach
- Oceanfront
- Fireplace/Heating
US $437/Night
For 7 Nights US $3,057
1250 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $368/Night
For 7 Nights US $2,575
People Visiting Longboat Key Also Like
Why Choose Rent By Owner for your Longboat Key Cottage Rentals?
What makes our Cottage Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Longboat Key
How to Book Your Longboat Key Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Longboat Key
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Longboat Key, FL
Jewfish Key
Beer Can Island
Longbeach Village
Quick Point Nature Reserve
Cannons Marina
Harborside Golf Course at Longboat Key Club
Islandside Golf Course at Longboat Key Club
Bay Isles
Longboat Key Beaches
Frequently Asked Questions About Longboat Key Rental Cottages
1. What are the top Cottages in Longboat Key?
There are a lot of options in Longboat Key. If you plan on staying in the Longboat Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Longboat Key:
- Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
- Take a peek awesome reviews 50 feet from sand
- 50 ft from sand, Private Island 125 +review
- Sun-Kissed Memories!
- 1 Week left April 18 of a kind home right on the beach then booked till July
- Client texted view crazy
- Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
- THE BEACH CONDO #107 BEACHFRONT FULL VIEW
- Unit #218 Sand Cay Beach Resort Gulf Front
- Upscale Beachplace Condo.availability starting in May 2026.please inquire
2. How many Cottages are available in Longboat Key?
Currently, the total number of properties listed by RBO in 2026 is over 4 in the Longboat Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Longboat Key.
More Rentals You May Like Near Longboat Key
1743.75 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Private Beach
- Oceanfront
- Fireplace/Heating
US $957/Night
For 7 Nights US $6,699
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4 Guests
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2 Bathrooms
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322.92 ft²
4 Guests
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4 Guests
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US $216/Night
For 7 Nights US $1,510
800 ft²
6 Guests
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1 Bathroom
Ocean View
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For 7 Nights US $2,806
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6 Guests
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1 Bathroom
Ocean View
Condo
- Fireplace/Heating
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US $370/Night
For 7 Nights US $2,592
800 ft²
6 Guests
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US $364/Night
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2000 ft²
8 Guests
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- Hot Tub
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- Fireplace/Heating
US $892/Night
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US $367/Night
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