
Cottage holiday rentals in Longboat Key
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Top-rated cottage rentals in Longboat Key
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday 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 hot tub

Sun Outdoors Sarasota, FL "Jungle Bridge Retreat"

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

Harbor Oasis - Hot Tub - Private

Sunny - Key West Vibe Cottage - Pool - Walkable

Beachy Keen Cottage A only steps to the Beach

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

Happy Camper Cottage | Cozy Oasis with Hot Tub

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail
Pet-friendly cottage rentals

Good Vibes Cozy Cottage on Million $ Row

The Pelicans Roost / Gulfport

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!

ALL NEW! Coral Sands II ~Coastal Modern 2/2 IRB
Private cottage rentals

Anna Maria Cottage w/Golf Cart

Palm Villa by Beach Boutique Rentals

Serene Island Cottage Waterfront Haven

2/2 Charming Riverfront Cottage w Deck & Kayaks

NEW 3BR Home w/ grill | Near AMI, IMG & Beach

Bayside Bliss: 1BR Cottage on Longboat Key

Guest Cottage on 5 Acres + On-Site Coffee Roastery

Cute Cottage, 2 min walk to beach, beach gear pool
Quick stats about cottage rentals in Longboat Key
Total rentals
20 properties
Nightly prices starting at
$181 NZD 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
Wi-Fi availability
20 properties include access to Wi-Fi
Destinations to explore
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- Rentals with a patio Longboat Key
- Family-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