Cottage vacation rentals in Longboat Key

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Top-rated cottage rentals in Longboat Key

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Guest favorite

Cottage in Tampa

4.99 out of 5 average rating, 145 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, smart TV’s, blackout curtains,shampoo/conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Pet fee $50. Elope/Proposal packages IG lakepossibility

Guest favorite

Cottage in Madeira Beach

4.91 out of 5 average rating, 116 reviews

Flipper's @ Mad Beach Cottage

Flipper's at Mad beach is a few steps away from the sugary sands of Madeira Beach, and close by the famous John's Pass Village & Boardwark where shopping and entertainment is always great. Completely renovated with light porcelain tile, nice furniture, queen bed with memory Thempur-Pedic mattress, exquisite modern shower, tall kitchen cabinets with plenty of storage. Huge private paved fenced backyard with gazebo, great for entertainment and outdoor grilling. You will love the beach decor.

Guest favorite

Cottage in Bradenton

4.93 out of 5 average rating, 304 reviews

Historic Private King Bed Suite-Near Beach-D’Town.

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 7:30AM. Please respect others. Walk to many great restaurants!

Guest favorite

Cottage in Bradenton Beach

4.96 out of 5 average rating, 142 reviews

Bradenton Beach Sunsets 3, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 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.

Guest favorite

Cottage in Myakka City

4.99 out of 5 average rating, 114 reviews

NEW! Peaceful Country Cottage near Lakewood Ranch

Enjoy the peace and solitude of the country at this fully renovated cottage. "Country Oaks" Cottage located on seven acres surrounded by nothing but woods and wildlife. We are located approximately 15 miles east of I-75 where you can enjoy privacy away from the bustling city but close enough to enjoy shopping and restaurant options in nearby Lakewood Ranch. Enjoy a trip to historic Arcadia for antique shopping or adventure out to Myakka State Park or TreeUmph! or even local beaches.

Guest favorite

Cottage in Indian Rocks Beach

4.93 out of 5 average rating, 179 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

Guest favorite

Cottage in Sarasota

4.94 out of 5 average rating, 141 reviews

Sea-esta Cottage-cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Fresh Market & Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

Guest favorite

Cottage in Nokomis

4.98 out of 5 average rating, 124 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Bella Vita! (The Good Life!)…that feeling when you wake up each day in this little slice of Paradise. This is the spot to enjoy a warm peaceful getaway from the rest of the world...just arrive with your bathing suit/flip flops and walk 1.5 blocks to the warm Gulf waters. Tranquillity of beach life, beautiful sunsets and lazy days of fishing and bird watching. Visit the Jetties, where you can see dolphins, manatees and rays, is only 1/2 mile away.

Superhost

Cottage in Siesta Key

4.84 out of 5 average rating, 133 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, stocked with everything but your clothes and toothbrush.

Guest favorite

Cottage in Bradenton

4.94 out of 5 average rating, 153 reviews

Cozy Cottage L-Steps to Riverwalk/Close to Beaches

Beautiful cottage style duplex located in Old Downtown West Bradenton in Historic Point Pleasant neighborhood - steps from Riverwalk! Close to beaches!!! Visit RealizeBradenton website for a listing of monthly events , Comfortably sleeps 4 - 1 bedroom with king size bed ,Living area has queen sleeper sofa, Kitchen: well equipped • Guest must disclose if they are bringing a pet and the pet breed • $50 per each 2-7 day stay - per pet

Guest favorite

Cottage in Treasure Island

5.0 out of 5 average rating, 178 reviews

Island Time Stay: Sunset

Fantastic find! This one bedroom, one bathroom cottage is located on Gulf Blvd in Treasure Island, Florida. It is located less than 300 steps from the beautiful sand of Treasure Island Beach and 5 blocks from the world famous boardwalk, shopping and restaurants of John’s Pass in Madeira Beach. Come soak up the sun and sand in this relaxing retreat. The Tampa Bay area is wonderful for year round golf...bring your clubs!

Guest favorite

Cottage in Anna Maria

4.98 out of 5 average rating, 209 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.