Longboat Key Cottage Rentals
Cottage
9.2(41 Reviews)
3 Bedrooms
2 Baths
6 Guests
1200 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $418/Night
7 Nights - US $2,923
House
2 Bedrooms
2 Baths
6 Guests
2002.09 ft²
- Oceanfront
Hot Tub
Pool- Ocean View
US $488/Night
7 Nights - US $3,416
Cottage
10.0(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $228/Night
7 Nights - US $1,595
Cottage
2 Bedrooms
2 Baths
4 Guests
1168 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $411/Night
7 Nights - US $2,879
New
Condo
2 Bedrooms
2 Baths
6 Guests
1623 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $226/Night
7 Nights - US $1,582
Apartment
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
1259.38 ft²
Private Pool
Private Beach- Oceanfront
- Fireplace/Heating
US $283/Night
7 Nights - US $1,981
US $1,134/Night
7 Nights - US $7,938
Condo
10.0(208 Reviews)
1 Bedroom
1 Bath
6 Guests
800 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $493/Night
7 Nights - US $3,451
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
322.92 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
US $254/Night
7 Nights - US $1,779
Condo
10.0(134 Reviews)
1 Bedroom
1 Bath
6 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $609/Night
7 Nights - US $4,265
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
333.68 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
US $437/Night
7 Nights - US $3,057
Condo
10.0(126 Reviews)
1 Bedroom
1 Bath
4 Guests
330 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $401/Night
7 Nights - US $2,808
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
Longboat Key Cottage Rentals Frequently Asked Questions
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
- 50 ft from sand, Private Island 125 +review
- Island Time on LBK: Open Sunday, $225/nt + Fees!
- Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
- Unit #218 Sand Cay Beach Resort Gulf Front
- Upscale Beachplace Condo.availability starting in May 2026.please inquire
- Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!
- Unit #210 Sand Cay Beach Resort Pool View
- Unit #110 Sand Cay Beach Pool View
- Beachcomber unit 204
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
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
6 Guests
699.65 ft²
- Private Beach
- Oceanfront
- Pool
- Ocean View
US $418/Night
7 Nights - US $2,926
Condo
10.0(94 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $526/Night
7 Nights - US $3,683
Apartment
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1743.75 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
US $957/Night
7 Nights - US $6,699
Condo
10.0(68 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $585/Night
7 Nights - US $4,097
Apartment
10.0(1 Review)
21 Bedrooms
2 Baths
4 Guests
1194.79 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
US $411/Night
7 Nights - US $2,877
Condo
10.0(38 Reviews)
2 Bedrooms
2 Baths
4 Guests
1503 ft²
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
US $229/Night
7 Nights - US $1,603
Condo
10.0(36 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $433/Night
7 Nights - US $3,030
Condo
10.0(24 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Kitchen
US $407/Night
7 Nights - US $2,847
Condo
10.0(22 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $531/Night
7 Nights - US $3,719
Condo
10.0(12 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $542/Night
7 Nights - US $3,797
Condo
10.0(12 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $465/Night
7 Nights - US $3,253
Condo
10.0(12 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $404/Night
7 Nights - US $2,831
