
Cottage vacation rentals in Longboat Key
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Longboat Key
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key cottage rentals
Cottage rentals with a pool

Coral Cottage pool/firepit 2 bedr 2 bth sleeps 6

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool

Family Friendly Beach Cottage in Madeira Beach, FL

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Historic 1930s Palmetto Cottage

Bayside Bliss: 1BR Cottage on Longboat Key

Charming cottage w/heated pool in prime location.

Drift Inn B Heated Pool & Private Beach Access!
Cottage rentals with a hot tub

Charming Home w/ Hot Tub, 20 min to Beach + Garden

Harbor Oasis - Hot Tub - Private

Beachy Keen Cottage A only steps to the Beach

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

Close to the Beach+ Private heated pool and spa!

Happy Camper Cottage | Cozy Oasis with Hot Tub

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

Hidden Oasis #1, hot tub near the beach
Pet-friendly cottage rentals

Good Vibes Cozy Cottage on Million $ Row

The Pelicans Roost / Gulfport

Family-Friendly Beach Cottage Manasota Key

Artsy guest house; near downtown w/ private patio

Adorable Dog-Friendly Cottage in Quaint Dunedin

Vintage Florida Beach Cottage B

Casa Azul. 2 bed/2 bath on lake

Gulfport Art District - One Block From Beach!
Quick stats about cottage rentals in Longboat Key
Total rentals
20 properties
Nightly prices starting at
€ 94 before taxes and fees
Total number of reviews
150 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Wifi availability
20 properties include access to wifi
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- Kid-friendly rentals Longboat Key
- Rentals with a fire pit Longboat Key
- Rentals with a patio Longboat Key
- Family-friendly rentals Longboat Key
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- Pet-friendly rentals Longboat Key
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- Rentals with a hot tub Longboat Key
- Rentals with a fireplace Longboat Key
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Lido Key Beach
- Cortez Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park