
Cottage vacation rentals in Casey Key
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Casey Key
Guests agree: these cottages are highly rated for location, cleanliness, and more.

Unit #2 Free bikes/kayaks/walk to beach/2bed/2bath
Unit # 2 Beautiful 2 bedrooms 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!
4.9 out of 5 average rating, 211 reviews
1930s Cottage + Pool 12 miles to Beach
Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.
4.95 out of 5 average rating, 128 reviews
Siesta Key Cozy Cottage across from the beach!
Adorable totally renovated !!!Siesta key cottage one block from the beautiful white sand beach and two blocks from the iconic Siesta Key Village on the north end of the island. Everything is a short walk including all the shops and restaurants of Siesta Village. Very private fenced in yard with plenty of comfy furniture and barbecue:) Very nice size stainless steel/granite kitchen with a dining room and a large sunken living room. Both the living room and the bedroom open to the private patio!
4.91 out of 5 average rating, 208 reviews
Adorable Cozy Silver Sands Cottage on Siesta Key!!
Wake up with a few minutes' walk to the world-famous, white crystal sand Siesta Key Beach with access across Midnight Pass Rd. Return to a bayside, quaint cottage with a heated pool, Tiki hut, fishing pier, & boat basin, directly on the Intracoastal Waterway. One of a few remaining small communities with Old Florida charm. Ground floor with close, free parking. Open porch swing. Blackout shades in BR, WiFi, high-def tv's, Keurig & reg coffee maker, full kitchen, outdoor shower.
4.88 out of 5 average rating, 201 reviews
Quaint Cottage,150 steps away from Crescent Beach!
Nestled on the serene Crescent Street, this classic 1969 cottage, is just a short walk to the ground quartz sands of Siesta Key. The 500 sq foot private brick paver and stone backyard off the screened in lanai is fully fenced with custom built stainless outdoor kitchen, featuring a large grill, refrigerator, custom built stone bar with seating for 8 . Nearby is a blue glass gas fire pit with a seating area, over sized (9 ft. diameter) in ground "spool", loungers and a large circular daybed.
4.99 out of 5 average rating, 115 reviews
Waterfront Retreat• Private Pool• Golf• Ping Pong!
Dive into the ultimate summer getaway! Relax at this cozy waterfront cottage with a private pool, & a short drive to AMI’s white-sand beaches. 2BR/2BA with two living areas include a bright Florida room overlooking the canal. Enjoy ping pong and a putting green ⛳. Start your mornings with coffee on the dock, watching fish jump out of the water. Fast WiFi, workspace, beach gear, and a kitchen with cooking essentials. Perfect for beach days, family getaways, or a relaxing coastal escape.
4.94 out of 5 average rating, 175 reviews
Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub
4 separate BRAND NEW inside (renovated 12/24) 2 bedroom/2 bath (+Queen Sofa Bed+ Chair/Bed) pool homes (Each sleeps 7) ONLY A 4 MINUTE WALK TO SIESTA KEY BEACH #1 in USA (no major streets to cross): First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Smart TV’s in all rooms, fine linens, towels, bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. Running/Walking: You have miles of beach to take in!
4.8 out of 5 average rating, 158 reviews
Bradenton Beach Sunsets 2, Anna Maria Island, FL
NO BOOKING FEE! Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.
4.98 out of 5 average rating, 262 reviews
Private Heated Pool Casita Near Downtown & Beaches
Charming and Cozy Casita Verde blends classic vintage charm with modern comforts. This 2-bedroom, 1-bath home features a 55" flat-screen TV with HD cable and fast Wi-Fi. Relax by the private pool or enjoy peaceful evenings on the deck with your favorite drink. Pet-friendly and conveniently located near Downtown Sarasota on Bahia Vista, with an easy drive to Lido Key, world-famous Siesta Key, and I-75 for day trips and longer adventures. 🌴 Cert# VR24-00152
4.93 out of 5 average rating, 156 reviews
Darling Old Florida Beach Cottage Steps From Gulf!
Completely Remodeled! Welcome to Cottage By The Sea, a newly remodeled charming retreat just steps from the pristine Gulf of Mexico beaches on Anna Maria Island, nestled in the serene area of Bradenton Beach. This delightful getaway blends the nostalgic charm of one of the only "Old Florida" cottages left, with modern updates, featuring bright and sunny décor. It's time to leave your worries behind and embrace the tranquility of paradise!
4.98 out of 5 average rating, 181 reviews
Staycation Sanctuary
Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!
4.98 out of 5 average rating, 189 reviews
Quaint Cottage w/access to Peace River canoe/kayak
This 2.2 cottage located on 10+ acres features waterfront view and ample parking. Tranquility and paradise intersect here. There are multiple buildings on site, so you may see other guests. There are kayaks and canoes on property. First come first serve. There is a boat ramp on property you are welcome to use for boats or kayaks. No smoking and No animals. We are a farm, so we cannot allow outside animals to the property.
4.99 out of 5 average rating, 134 reviewsPopular amenities for Casey Key cottage rentals
Cottage rentals with a hot tub

Charming Coastal Oasis 2 Bed/2 Bath Cottage
4.94 out of 5 average rating, 51 reviews
Close to the Beach+ Private heated pool and spa!
4.95 out of 5 average rating, 84 reviews
Sarasota Cottage Near Beaches, Downtown & Airport
5.0 out of 5 average rating, 14 reviews
Over the Moon
5.0 out of 5 average rating, 6 reviews
Cozy Cottage 1 block from Beach
4.92 out of 5 average rating, 78 reviews
Charming Home w/ Hot Tub, 20 min to Beach + Garden
4.95 out of 5 average rating, 58 reviews
Lake Ibis Retreat-Resort Perks Included
5.0 out of 5 average rating, 3 reviews
Cozy Cottage Near Siesta Key Village!
4.71 out of 5 average rating, 7 reviewsPet-friendly cottage rentals

Cortez ~ Grouper Cottage. BRING YOUR BOAT!
4.98 out of 5 average rating, 117 reviews
Ohana Gulfside C Historic 1 Bed - 250 ft. to Beach
4.9 out of 5 average rating, 217 reviews
River Cottage 2/2 - Kayaks & Huge Deck-Old Florida
4.97 out of 5 average rating, 73 reviews
Walk to the beach! Clean remodeled 3 bed Cottage
4.8 out of 5 average rating, 15 reviews
Happily Ever After
4.99 out of 5 average rating, 73 reviews
Chic Peaceful 3BD Cottage - Walk to Siesta!
4.73 out of 5 average rating, 22 reviews
1 Bed-Walk beach-bikes-kayaks-grill-out hot shower
5.0 out of 5 average rating, 45 reviews
Lakefront/Private Pool on 5 Acres Lakewood Ranch
4.94 out of 5 average rating, 18 reviewsPrivate cottage rentals

Romantic Getaway “Waterside” Dockage~Canal front
4.99 out of 5 average rating, 145 reviews
Cottage on Siesta Key Beach
4.88 out of 5 average rating, 349 reviews
Mattie’s Cottage by the Bay
4.94 out of 5 average rating, 96 reviews
Manasota Beach Cottage
5.0 out of 5 average rating, 47 reviews
Studio by Lido Beach w heated pool
4.93 out of 5 average rating, 57 reviews
Bee Keepers Cottage
4.97 out of 5 average rating, 75 reviews
Private Beach at Aloha Kai
4.89 out of 5 average rating, 54 reviews
Zen Cottage in Museum District Walk to Bay Sunsets
4.85 out of 5 average rating, 80 reviewsDestinations to explore
- Miami Vacation rentals
- Four Corners Vacation rentals
- Miami Beach Vacation rentals
- Orlando Vacation rentals
- Fort Lauderdale Vacation rentals
- Panama City Beach Vacation rentals
- Tampa Vacation rentals
- Hollywood Vacation rentals
- Jacksonville Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Cape Coral Vacation rentals
- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Island Beach
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Caspersen Beach
- Vinoy Park
- Manasota Key Beach
- John's Pass
- Tropicana Field
- Englewood Beach
- Crescent Beach
- Img Academy
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Cortez Beach
- Fort De Soto Park
- North Beach At Fort DeSoto Park
- Myakka River State Park
- Lido Beach
- Stump Pass Beach State Park





