Cottage holiday rentals in Englewood

Explore the key, Walk to beach, bikes & kayaks

Welcome to your perfect beach escape on Manasota Key! This charming 1-bedroom cottage is just a 3-minute stroll from sandy shores and stunning Gulf sunsets. Enjoy all the comforts of home, including a grill, shared laundry and cozy back patio. Located in a peaceful neighborhood with easy access to parks, kayaking, and waterfront dining. Kayaks, bikes, beach chairs, umbrella, towels and a cooler are provided for your use. Relax, explore, and make unforgettable memories in this beautiful paradise!

Romantic Getaway “Waterside” Dockage~Canal front

Also available: airbnb.com/h/aframeausable Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. There is a dock available here. Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources! Jug Creek Marina is steps away with food & music!

Manasota Beach Cottage

Vintage Beach Cottage on the Southern end of Manasota Key...just 30 steps from the Beach. Spectacular sunsets from your living room and screen porch. Sitting on one and a half lots with plenty of parking and room for your RV.! The front bedroom has a king size bed and great gulf views. There is also a queen sleeper in the living room and bunk beds off the kitchen. Fully equipped kitchen, full new bathroom with walk in shower, and all new furnishings. Bikes, beach chairs, and umbrellas!

Mattie’s Cottage by the Bay

Enjoy this 1913 Florida vernacular cottage! Carefully restored, thoughtfully updated house on a quiet, tree-canopied street in historic Osprey, one of Sarasota County’s oldest settlements. Enclosed front porch, screened back porch, and tin roof. Walk to the bayfront, restaurants, shopping, library, parks, and historic sites. A short drive takes you to famous Gulf beaches and all Sarasota and Venice have to offer. Hurricane Milton: Yes, we are cleaned up and have power and internet!

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!

Magnolia Cottage

Enjoy the walking-distance restaurants, shops and bars from this cozy cottage in the heart of Olde Englewood. Catch fish or the sun dancing on the water at Lemon Bay just two blocks away. The neighborhood is great for morning and evening strolls. Four local beaches are just minutes away. Relax with a refreshing beverage on the back patio, fenced for your privacy. If you want to park the car and enjoy a quaint beach town without the hassle, we have you covered!

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!

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.

Bamboo Cottage, minutes to beach, no guest fee!

We pay Airbnb's Guest Fee. Save on Weekly and Monthly Stays! Discount automatically applies :). Welcome to The Bamboo Cottage! A peaceful and private 1940's Old Florida farmhouse tucked away in Englewood's Historical District. Centrally located within walking distance to Dearborn Street & Lemon Bay, and just miles to the beautiful beaches of Manasota Key!