Cottages in Clearwater, FL at the best prices

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Clearwater, FL cottages
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88 Best cottages in Clearwater, FL

Best family friendly Clearwater, FL cottage rentals

Among the 88 accommodations in Clearwater, FL, here are the 4 best family friendly cottage rentals

Chic Cottage Walk To Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3 - Clearwater, FL
10 32 reviews

Chic Cottage Walk To Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3

cottage, Dunedin
This Dunedin seaside cottage, near BayCare Alliant and Mease Dunedin Hospitals (under 1.6km away), offers stunning sea views and easy beach access, plus proximity to SimCenter Tampa Bay and Dunedin Marina (within 1.6km).
The 79 square metre property sleeps six, boasting two bedrooms, one bathroom, a fully equipped kitchen (including dishwasher), air conditioning, a terrace, garden, and even a private tennis court.
Caribbean Vive Across The Gulf  Beach. - Clearwater, FL
10 34 reviews

Caribbean Vive Across The Gulf Beach.

cottage, Indian Rocks Beach
This charming beachfront cottage is situated just a short 3-minute walk from the sands of Indian Rocks Beach, offering easy access to the water and the vibrant atmosphere of the local area. It consistently receives excellent reviews from guests, highlighting its comfortable and convenient location.
The cottage is available as a single unit or as a whole house, perfect for families or groups. It boasts a modern nautical design, a private garden oasis with a hammock and swing, and a shared patio with BBQ facilities, seating for 14, and beach gear. Guests can also enjoy the on-site swimming pool, jacuzzi, and spa, as well as explore the local attractions and water activities.
Enchanting Cottage With Ac In Palm Harbor - 2 Bedrooms, 1 Bathroom & Hot Tub - Clearwater, FL
9.8 23 reviews

Enchanting Cottage With Ac In Palm Harbor - 2 Bedrooms, 1 Bathroom & Hot Tub

cottage, Palm Harbor
This Palm Harbour holiday home is situated a 4.5km drive from Innisbrook Golf Club and 1.9km from Curlew Crossing Shopping Centre, offering easy access to Tampa Bay, Clearwater Beach, and Old McMickey's Farm.
The 58 square metre self-catering property features two bedrooms, one bathroom, and sleeps four, including a fully equipped kitchen, Jacuzzi, air conditioning, Wi-Fi, in-unit laundry, and barbecue facilities.
Paradise By The Gulf ~ Unit A ~ 460 Steps To The Beach - Private Swim Spa Home. - Clearwater, FL
10 2 reviews

Paradise By The Gulf ~ Unit A ~ 460 Steps To The Beach - Private Swim Spa Home.

cottage, Indian Rocks Beach
This detached house is centrally located in Indian Rocks Beach, a short walk from the beach, local cafes, bars, and shops, and approximately 10 kilometres from John's Pass Village and Boardwalk.
This family-friendly detached house sleeps up to eight guests across three bedrooms and two bathrooms, featuring a private swim spa, a swimming pool, air conditioning, and a fully equipped kitchen.

Best Clearwater, FL cottages with a garden

Escondido Boutique Bungalow In Crystal Beach- Inquire For Seasonal Savings! - Clearwater, FL
10 34 reviews

Escondido Boutique Bungalow In Crystal Beach- Inquire For Seasonal Savings!

cottage, Palm Harbor
This charming cottage is situated just a short distance from Palm Harbor, within easy reach of both Innisbrook Golf Club and Wall Springs Park, making it ideal for exploring the local area. The property enjoys an excellent user rating, reflecting its popularity amongst previous guests.
The cottage offers two bedrooms and one bathroom, providing comfortable accommodation for up to four guests. You'll find a range of amenities on offer, including a fully equipped kitchen, a private fenced yard, barbecue grills, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
3 Mi To Beach: Modern Retreat In Largo! - Clearwater, FL
10 1 review

3 Mi To Beach: Modern Retreat In Largo!

cottage, Largo
This detached house in Largo is located less than 1 kilometre from Largo Medical Centre and The Amish Country Store, and within 5 kilometres of Belleview Biltmore Golf Club and Serenity Gardens Memorial Park.
This detached house offers air conditioning, a swimming pool, a garden, free parking, and a well-equipped kitchen with a microwave and dishwasher, alongside complimentary WiFi in public areas and barbecue grills for al fresco dining.
6 Mi To Clearwater Beach: Home W/ Furnished Lanai - Clearwater, FL
No reviews

6 Mi To Clearwater Beach: Home W/ Furnished Lanai

cottage, Clearwater
This detached holiday home in Clearwater is situated 322 metres from Eagle Lake Park and within 4.8 kilometres of Morton Plant Hospital and Largo Central Park.
The property offers air conditioning, a swimming pool, a garden, and a well-equipped kitchen with a microwave and dishwasher, alongside barbecue grills for outdoor dining.
Best Location! Walk To Dining, Trail & Stadium - Clearwater, FL
9.9 261 reviews

Best Location! Walk To Dining, Trail & Stadium

apartment, Dunedin
This dog-friendly cottage is located just 0.5km from the waterfront and downtown Dunedin, within easy walking distance of the Pinellas Trail, the library, and the Blue Jays' stadium. The cottage has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom, one-bathroom property offers 64 square metres of space and can accommodate up to four guests. The cottage features a well-equipped kitchen, a sunny living/dining area, a private patio, a sheltered terrace, and a shared laundry facility.

Frequently Asked Questions about cottages in Clearwater, FL

  • What would be a good 2-days itinerary for visiting Clearwater, FL?

    On your first day, head to Clearwater Beach and spend the afternoon on the sand. In the evening, visit Pier 60 for the sunset celebrations and street performers. The next day, explore the Clearwater Marine Aquarium, home to Winter the dolphin, and enjoy the Clearwater Beach Walk, a scenic promenade with shops and restaurants.
  • What are the best cottage rentals in Clearwater, FL?

  • What part of Clearwater, FL is ideal for renting a cottage?

    The best area for renting a cottage in Clearwater is the Clearwater Beach area. It's a charming area with many beautiful cottages that are close to the beach, restaurants and shops. You'll find plenty of options in the area, from cozy cottages to larger ones with private pools.
  • What are the best cottage rentals with a pool in Clearwater, FL?

  • When is the best time to rent a cottage in Clearwater, FL?

    The best time to visit Clearwater is in the spring or autumn. The weather is pleasant and the crowds are smaller. If you want to experience the warm weather and enjoy the beach, the summer months are also a good option, but be prepared for larger crowds and higher prices.
  • What are the best cottage rentals with a jacuzzi in Clearwater, FL?

  • What are the can't-miss sights in Clearwater, FL?

    You must visit Clearwater Beach, a stunning stretch of white sand known for its beautiful sunsets and clear waters. The Clearwater Marine Aquarium is another must-see, home to Winter the dolphin. For a unique experience, take a boat trip to see the dolphins in the wild.
  • What are the best cottage rentals for families and kids in Clearwater, FL?

  • Why consider renting a cottage in Clearwater, FL for your stay?

    Renting a cottage in Clearwater allows you to experience the charm of the area and enjoy a more relaxed and private stay. Cottages often come with amenities like a private patio or balcony, a fully equipped kitchen, and a washing machine and dryer. You'll also find that cottages are often located in quieter areas, providing a peaceful retreat from the hustle and bustle of the city.
  • What are the best pet friendly cottage rentals in Clearwater, FL?

  • Can you easily explore Clearwater, FL on foot or by bike?

    Clearwater Beach is easily explored on foot or by bike, particularly the area around Pier 60. There are also bike paths along the waterfront and through the city. If you're exploring further afield, consider renting a car or using the local bus service.
  • What are the best cottage rentals with parking in Clearwater, FL?

  • What are the best restaurants in Clearwater, FL with nature views?

    For stunning waterfront views, try Frenchy's Rockaway Grill, located right on the beach. Another great option is the Clearwater Beach Cafe, which offers views of the Gulf of Mexico. If you're looking for a more upscale experience, try the Palm Pavilion, which has a beautiful outdoor patio overlooking the beach.
  • What family-friendly activities are available in Clearwater, FL?

    Clearwater is a great destination for families. Visit the Clearwater Marine Aquarium to see Winter the dolphin, take a dolphin-watching tour, or spend a day at the beach. For a fun day out, visit the Suncoast Primate Sanctuary or the Clearwater Beach Marine Aquarium.

Popular destinations

Best Clearwater, FL cottage rentals with jacuzzi

Among the 88 accommodations in Clearwater, FL, here are the 4 best cottage rentals with a jacuzzi

Cozy And Roomy Cottage - Clearwater, FL
10 75 reviews

Cozy And Roomy Cottage

cottage, Dunedin
This charming cottage is conveniently located in Dunedin, just under 2 kilometres from SimCenter Tampa Bay and Mease Dunedin Hospital, and within 3 kilometres of Dunedin Marina and Dunedin Fine Art Center. It has received excellent reviews from previous guests, making it a popular choice for visitors to the area.
The cottage is a comfortable and well-equipped self-catering property, spanning 74 square metres and accommodating up to two guests. It has everything you need for a relaxing stay, including a fully equipped kitchen, laundry facilities, a private patio, a fireplace, a swimming pool, a spa, a tennis court and much more.
Island Estates Updated 2 Bed 2 Bath Water Views A Short Walk To Clearwater Beach - Clearwater, FL
10 2 reviews

Island Estates Updated 2 Bed 2 Bath Water Views A Short Walk To Clearwater Beach

cottage, Clearwater
This ground-floor apartment is located in Island Estates, Clearwater Beach, just a block from the Clearwater Aquarium and a short walk from a Publix supermarket. It has received excellent reviews from previous guests.
This two-bedroom, two-bathroom apartment is 84 square metres in size and can accommodate up to two guests. It features a fully-equipped kitchen, a private patio, a jacuzzi, a garage, and access to a boat dock and lift.
Tiki Hut In Tropical Paradise - Clearwater, FL
10 28 reviews

Tiki Hut In Tropical Paradise

cottage, Dunedin
This charming cottage is conveniently located in Dunedin, just 1.6km from SimCenter Tampa Bay and Mease Dunedin Hospital, and within 3.2km of the Dunedin Fine Art Center and Dunedin Marina. The property has received excellent user ratings and is ideal for a relaxing getaway.
The cottage sleeps up to 4 guests and offers two bedrooms and two bathrooms. Guests can enjoy a private outdoor pool, a spa tub, a fully equipped kitchen, a laundry room, a patio, and a tranquil garden setting.
Key West Style Cottage - With Pool/hot-tub - Clearwater, FL
9.8 15 reviews

Key West Style Cottage - With Pool/hot-tub

cottage, Dunedin
This charming cottage in Dunedin is ideally situated just a short walk from the town's lively restaurants and bars, making it a perfect base for exploring this vibrant area. The cottage is highly rated by previous guests, ensuring a comfortable and enjoyable stay.
The cosy cottage provides a comfortable king-size bed and a private bathroom, ideal for couples seeking a relaxing retreat. Guests can enjoy a range of amenities including a shared lounge area, a swimming pool, a hot tub, and free parking.

Best pet friendly Clearwater, FL cottage rentals

Among the 88 accommodations in Clearwater, FL, here are the 4 best pet friendly cottage rentals

Cozy Clearwater Getaway  10 Mins To Beach - Clearwater, FL
No reviews

Cozy Clearwater Getaway 10 Mins To Beach

cottage, Largo
This Largo apartment, situated approximately 16 kilometres from Clearwater Beach, provides easy access to Clearwater's attractions, including Jack Russell Stadium and Florida Auto Exchange Stadium.
The two-bedroom, one-bathroom flat sleeps two guests and features a kitchen with fridge, microwave, and dishwasher, air conditioning, parking, internet access, and a private gated outdoor space with a hot tub.
Poolside Oasis! Family Escape In Safety Harbor - Clearwater, FL
10 1 review

Poolside Oasis! Family Escape In Safety Harbor

cottage, Safety Harbor
This holiday home is located in the North Bay Hills district, within 3 kilometres of Tampa Bay, Philippe Park, and Mease Countryside Hospital, and 4 kilometres from Westfield Countryside mall.
This detached house offers a private outdoor swimming pool, a video game room, and a fully equipped kitchen with a microwave oven and dishwasher, with parking and internet provided.
Downtown Dunedin Cottage  Walk To Restaurants - Clearwater, FL
10 82 reviews

Downtown Dunedin Cottage Walk To Restaurants

cottage, Dunedin
This Dunedin cottage, located in the Downtown area, is less than 2km from both BayCare Alliant Hospital and Mease Dunedin Hospital, and within 1.6km of Dunedin Marina and Dunedin Stadium.
The 45 square metre self-catering property sleeps three, offering a bedroom, bathroom, fully equipped kitchen with appliances including a washing machine, free Wi-Fi, private patio, and on-site playground.
Cottage By The Gulf - Clearwater, FL
10 60 reviews

Cottage By The Gulf

cottage, Dunedin
This charming cottage is situated in central Dunedin, just a short walk from the Blue Jays Spring Training Stadium and the Pinellas Trail, with the bustling downtown and the beach just 0.3 kilometres away. The cottage has received excellent reviews from previous guests and is perfect for families or groups of up to five people.
The cottage is spread over 102 square metres and has two bedrooms and two bathrooms, making it a comfortable and spacious retreat. The cottage includes a fully equipped kitchen, a private garden, a spa, and air conditioning, as well as a patio with outdoor seating, perfect for enjoying the Florida sunshine.
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