Cottage vacation rentals in Bay Pines

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Top-rated cottage rentals in Bay Pines

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Guest favorite

The entrance features a bright pink exterior, complemented by white trim and a welcoming white door labeled 'B.' Lush green plants are arranged on either side of the door, enhancing the cheerful appeal. A well-maintained artificial lawn lies in front, with a simple concrete pathway.

Cottage in Indian Rocks Beach

4.9 out of 5 average rating, 286 reviews

Vintage Florida Beach Cottage B

Just a short walk to the beach makes this a great beach getaway for couples or families. On your way you can stop at the Kooky Koconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2019, this unit is in updated, very clean and worry free condition. This cottage is located in a quiet residential neighborhood and a great place to relax. Common laundry on shared screened porch. Dogs allowed (extra $45 cleaning). Easy refund policy. Level 2 EV charger

Top guest favorite

Cottage in Pass-a-Grille Beach

4.97 out of 5 average rating, 144 reviews

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Guest favorite

A wide expanse of golden sand stretches toward the calm blue waters of the Gulf. Gentle waves can be seen in the distance, while colorful beach umbrellas dot the shoreline, creating a lively beach scene under a clear sky.

Cottage in Madeira Beach

4.84 out of 5 average rating, 128 reviews

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Top guest favorite

Cottage in Dunedin

4.96 out of 5 average rating, 205 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

Discover a charming 1920's cottage nestled in the heart of Dunedin, 3 blocks from the water and downtown. This delightful cottage is ideally located 2 blks from the Pinellas Trail, the Fenway Hotel, and the Blue Jay's stadium. Surrounded by lush greenery, the cottage boasts a private outdoor space perfect for you to enjoy your coffee. Inside, you'll find a sunny kitchen, a spacious living and dining area, and comfortable beds to ensure a wonderful stay. Come and enjoy a memorable stay here!

Guest favorite

Cottage in Dunedin

4.8 out of 5 average rating, 123 reviews

Serene French Country Cottage near everything

Unwind in this rustic French provençal, Extra Cosy Cottage w/ Unique Decor in Charming, Artsy Dunedin. Fenced in yard. Free Parking&Wifi. CENTRAL LOCATION Close to Clearwater Beach, Honeymoon Island. Short walk to Downtown Dunedin, Pinellas Trail, Blue Jay Stadium & Beautiful sunsets! Perfect location for Walkers, Runners and Bikers! A home away from home in a very convenient location for quality shopping, dining, nature explorations and beaches! A short walk or Uber away from everything!

Guest favorite

A wooden pergola frames a tranquil beachfront view, with two dark blue adirondack chairs positioned for relaxation. Soft green grass leads to sandy pathways that stretch toward the water, creating a calm outdoor spot for enjoying the coastal atmosphere.

Cottage in Indian Rocks Beach

4.77 out of 5 average rating, 102 reviews

#5 Beach Front Cottage w view- Indian Rocks Beach

LOCATION, location! Closest beach cottage to the water at Indian Rocks beach, view of the water from your porch & easy access to grass for pets. Perfect couples getaway. Enjoy some of Florida’s best beaches. Minimalistic living. *Kitchen recently updated* Shared gazebo & picnic table next door. Shared Washer & dryer takes quarters. Walking distance to local restaurants and bars. Minutes away from Clearwater beach, tourist attractions and mini golf. Property located next 2 public access.

Guest favorite

A serene beach scene showcases soft white sand meeting gently lapping waves under a clear blue sky. Dune grass and small green plants are visible in the foreground, adding a natural touch to the tranquil coastal setting.

Cottage in Indian Shores

4.96 out of 5 average rating, 146 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Superhost

A cozy living area features a mix of striped and solid blue seating arrangements, enhanced by wooden floors. Natural light enters through double doors leading to the outdoor space. A television is mounted on the wall, while a white coffee table sits centrally, inviting relaxation.

Cottage in Clearwater Beach

4.88 out of 5 average rating, 119 reviews

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

Guest favorite

A view of a sandy beach stretches toward calm blue waters under a clear sky. A wooden walkway leads from the beach access point, framed by green grass and beach plants. An umbrella and two figures are visible in the distance on the shore.

Cottage in Redington Shores

4.74 out of 5 average rating, 321 reviews

Below -Deck Studio Gulf Side 40 steps to the beach

An original beach cottage built in 1947. Only 40 steps to the Shores of Redington beach Florida. One free parking spot on premises in front of cottage-far left Pay public parking across from cottage. Seabreeze and wahoo restaurants on the bay 40 steps to the intercoastal is called the Narrows want to rent a kayak and paddle around the bay or take it 40 steps west put it in the Gulf of Mexico. surf shop to rent bikes or Kenny’s corner diner, frog pond broke n board foods

Top guest favorite

The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.

Cottage in Dunedin

4.97 out of 5 average rating, 301 reviews

Walk Downtown and Waterfront Barefoot Parrot 3

Discover coastal modern luxury in this stylish, spacious upstairs 2-bedroom cottage. Steps from Main Street Dunedin, enjoy nearby restaurants, shops, and breweries, or take a short walk to stunning waterfront sunsets. A quick drive to Honeymoon Island and Clearwater Beach, this pet-friendly retreat boasts two king beds, a sleeper sectional, and serene treetop views. Your bright, unforgettable coastal escape awaits—book your Dunedin getaway today!

Top guest favorite

A spacious cottage interior features a large white bed covered by a bright yellow blanket. Pastel-colored pillows add subtle contrast. The wall above the bed showcases vibrant pineapple artwork, while the room is illuminated by modern light fixtures. A cozy seating area is visible to the right.

Cottage in Treasure Island

5 out of 5 average rating, 191 reviews

Island Time Stay: Happy Hour

Check out our large studio cottage 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 Village in Madeira Beach. We have a crosswalk conveniently located in front of the property. You can stop traffic with the push of a button to safely walk across the street toward the boardwalk.

Top guest favorite

The exterior of a cottage features a welcoming yellow door and light blue accents under a sloped roof. Lush green landscaping surrounds a spacious front porch adorned with two colorful chairs. Tropical plants and palm trees enhance the vibrant atmosphere.

Cottage in Safety Harbor

4.96 out of 5 average rating, 179 reviews

Harbor Oasis with Hot Tub

In the heart of Safety Harbor, this cottage has easy access to Tampa, St. Pete, and Clearwater beaches. Completely renovated light and airy cottage with magnificent landscaping. Features a spa tub and very private fenced in backyard. This beautiful space is perfect for your perfect resort vacation within an exciting bayside town.