
Cottage rentals near Anna Maria Island
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Top-rated cottage rentals near Anna Maria Island
Guests agree: these stays are highly rated for location, cleanliness, and more.
Popular amenities for cottage rentals near Anna Maria Island
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 | Lush Backyard

Sunny - Key West Vibe Cottage - Pool - Walkable

Close to the Beach+ Private heated pool and spa!

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

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

Beach Dream Cottage: Private Pool and Spa!
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

Cozy up in a French Country nest NEAR EVERYTHING

Cozy Cottage by the Bay

Gulfport Art District - One Block From Beach!
Private cottage rentals

Drift Inn A Heated Pool & Private Beach Access!

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Hibiscus Villa by Beach Boutique Rentals

Shady Nook Beachfront Cottage

"Honeybee Hideaway" Cozy Cottage Near SIESTA KEY

Sailfish Gulf Suites #2, Beachfront, Steps to the

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

Cute Cottage, 2 min walk to beach, beach gear pool
Luxury cottage rentals

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool

3 Palms Beachfront Cottages - Beachfront

Location 3 Bed Cottage 1 block to SiestaKey beach

Charming Stand Alone Cottage! Walk 2 Beach/Bridge

Seashell Cottage

NEW! 2BR/2BA Finest Vacation Home Steps to Beach

Beachy Paradise

The All Hands On Deck Cottage at Casa Limonada
Quick stats about cottage rentals near Anna Maria Island
Total rentals
70 properties
Nightly prices starting at
$165 CAD before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool
Destinations to explore
- Rentals with a patio Anna Maria Island
- Waterfront rentals Anna Maria Island
- Hotel rentals Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Luxury rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Rentals with a firepit Anna Maria Island
- Rentals with beach access Anna Maria Island
- Beachfront rentals Anna Maria Island
- Bungalow rentals Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Rentals with a washer and dryer Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
- Beach condo rentals Anna Maria Island
- Rentals with pools Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Apartment rentals Anna Maria Island
- House rentals Anna Maria Island
- Kid-friendly rentals Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Rentals with lake access Anna Maria Island
- Villa rentals Anna Maria Island
- Condo rentals Anna Maria Island
- Beach house rentals Anna Maria Island
- Townhouse rentals Anna Maria Island
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