
Holiday rentals in Clearwater
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Top-rated holiday rentals in Clearwater
Guests agree: these stays are highly rated for location, cleanliness and more.

3 BR/2B pool home WiFI and Brand new furnishings
Lots to Love about this centrally located Clearwater beauty. This pool home is 25 minutes from the Tampa airport and 15 minutes to famous Clearwater Beach and less than a half hour to downtown St. Pete, not to mention a 10 minute walk to Phillies spring training stadium and minutes by car to hundreds of Shoppes and Restaurants. Enjoy this spacious home with split bedroom plan and brand new furnishings. Sweet dreams on the Casper mattresses. Relax Poolside in the screened lania or by the firepit

Clearwater Gameroom- Pool/Mini golf/Home Theatre
Welcome to Clearwater Hangout- This super unique house was designed to be packed with many amenities. Just 4mi to famous Clearwater Beach! Newly renovated with fresh tiles and quartz counters for a high end trendy design. Inside amenities include- LED vanity, pool tbl/ping pong, wine fridge, dining for 14, and a full transformed game room with a basketball court, Pac-man machine, and a home theatre! Outside is a very private clean space with mini golf, a salt water pool, seating area and firepit

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach
🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Walk to Downtown and Waterfront - Private Yard
Steps to Main Street and minutes to beaches, yet tucked away. Private yard with grill in a prime location. Stroll to restaurants, breweries, shops, and live music. Walk to gorgeous waterfront sunsets or drive minutes to award-winning beaches such as Honeymoon Island, Caladesi Island & Clearwater Beach. Designer decor. Sleeps 6. Two king bed suites and a luxury couch that sleeps 2 more. Fully loaded for kids, pets and sunny beach days! Treat yourself and book this Dunedin favorite today.

New private guesthouse walk to downtown Dunedin
This new construction (July, 2024) unique and tranquil unit is perfect for your weekend getaway or a longer stay. Light, bright and neutral, 10 foot ceilings make property feel more spacious. Very quiet and private, concrete block construction provides solid insulation. Close to Clearwater and Honeymoon Island beaches, walking distance to TD Ballpark .6 miles, downtown Dunedin 1.2 miles to shops and restaurants, Pinellas Trail is across the street, easy transit to airport.

Watch the Sunrise at Sunrise! @ Clearwater home.
Welcome to your perfect vacation getaway! Our beautiful home offers a heated pool, perfect for relaxing any time of year—whether you’re enjoying a sunny afternoon swim or a peaceful evening under the stars. The property features plenty of space for everyone to feel comfortable, both indoors and outdoors. With open living areas, comfortable furnishings, and a spacious layout, it’s ideal for families, friends, or groups looking to unwind and create unforgettable memories.

3 Bedroom Waterfront Paradise Sleeps 8
Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.

Ocean Breeze • Easy - Heated Pool Access
The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

Private Ocean View Beach Retreat with Balcony
Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Central Clearwater | 3BR Modern Retreat
Experience refined comfort in this beautifully designed home in central Clearwater near Drew St, minutes from beaches, dining, and shopping. The space features 1 King bed, 1 Queen bed, and a Twin-over-Queen bunk. Enjoy upscale touches including a PS5, elegant outdoor lounge with BBQ grill, washer & dryer in the master bath, and a Keurig coffee maker for effortless mornings.

Heated Pool Home | Close to Clearwater Beach
Enjoy a beautifully renovated 2BR/2BA Clearwater home with a private heated pool, BBQ, and outdoor lounge. Just 14 minutes from Clearwater Beach, restaurants, and shopping. Family-friendly with beach gear, pool toys, and high-speed WiFi. Perfect for a relaxing Florida getaway!
Popular amenities for Clearwater holiday rentals
Other great holiday rentals in Clearwater

Welcome to your vacation home

Tropical Paradise - Private Pool, Spa & BBQ !

Lux *Home MINS to *Beach*, *Hospital* & *Downtown*

CBC 1-7C- Beautiful Gulf Front Condo with Pool!

Game Room + Fire Pit Fun! • 2BR • 7 mi to Beach

Clearwater Mediterranean Retreat • Pool & Fire Pit

Organic & Modern~90° Heated Salt Pool~Walk 2 beach

2BR Clearwater Home w/ Heated Pool & Backyard Bar!
When is the best time to visit Clearwater?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $196 SGD | $238 SGD | $267 SGD | $221 SGD | $192 SGD | $192 SGD | $194 SGD | $178 SGD | $167 SGD | $168 SGD | $181 SGD | $191 SGD |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Frequently Asked Questions
What are the best places to stay in Clearwater?
Clearwater Beach is known for lively boardwalks and waterside views, while the downtown area has a mix of cultural sites and dining spots. Nearby, Sand Key offers a quieter atmosphere with access to parks and nature.
What are the best things to do in Clearwater with kids?
Families often explore Clearwater Beach, stop by the marine aquarium to learn about sea life, or enjoy playgrounds and shaded picnic areas in local parks. Interactive exhibits and boat tours are also frequently suggested.
What are some of the best things to do in Clearwater?
Clearwater has lively beaches, fresh seafood restaurants, and sunset festivals on the pier. Visitors also explore local art galleries, dolphin-watching tours, and nearby nature preserves.
How is the weather in Clearwater?
Clearwater has mild winters around 56–74°F (13–23°C) and hot, humid summers that can reach 91°F (33°C). Rainfall increases in the summer months, so packing a light rain jacket and sun protection is often wise.
What are the best places to visit in Clearwater?
Clearwater Beach is one of the most popular waterfront areas, while Pier 60 draws many for its sunset festivals and street performers. Nature lovers frequently explore Sand Key Park and local nature reserves.
What are some hiking trails in Clearwater?
Explore nature trails in local parks such as Moccasin Lake Nature Park, or stroll boardwalks by the water around Sand Key Park. These areas often feature shaded paths and bird-watching opportunities.
What are some family activities we can do in Clearwater?
Family groups enjoy Clearwater Marine Aquarium's animal care programs, miniature golf courses, and scenic public playgrounds. On the beach, sandcastle building and paddleboarding are frequently suggested.
What are some of the best day trip ideas from Clearwater?
Many guests explore nearby cities with art centers, botanical gardens, or aquariums. Guided boat tours along the coast, nature preserves just outside Clearwater, or state parks are also frequently suggested.
Are there any pet friendly accommodations available in Clearwater?
Many stays in Clearwater welcome pets, especially around the beach and in quieter residential neighborhoods. Several parks and walking trails make it convenient to travel with your dog.
What are some local tips for visiting Clearwater?
Arrive at popular beaches early for shaded spots, and bring sun protection year-round. Local markets are great for unique souvenirs, and many restaurants accommodate dietary preferences if you ask in advance.
What is Clearwater known for?
Clearwater is known for its sandy Gulf beaches, vibrant sunset celebrations at Pier 60, and marine preservation work at the local aquarium. Its festivals and outdoor concerts reflect a lively coastal spirit.
What are the best hidden gems to explore in Clearwater?
Moccasin Lake Nature Park is often mentioned for quiet trails and educational centers, while local farmers markets showcase regional produce and crafts. Small art galleries around downtown highlight area artists.
What are the best foods to try in Clearwater?
Fresh grouper sandwiches, stone crab when in season, and citrus-inspired desserts are frequently suggested. Many restaurants feature seafood caught nearby, often served with a coastal flair.
What should I bring for a trip to Clearwater?
Bring lightweight clothing, reef-safe sunscreen, a reusable water bottle, and swimwear. A wide-brimmed hat and comfortable sandals are helpful for sun protection and boardwalk strolls.
What is the nightlife in Clearwater like?
Nightlife in Clearwater centers around casual beachfront bars, live music venues, and vibrant spots for dancing. Some local breweries and rooftop lounges also draw evening crowds.
What are the most popular events or festivals in Clearwater?
Clearwater has the Pier 60 sunset festival with live music and artisans, the Clearwater Jazz Holiday in fall, and parades celebrating local traditions. Seafood events also draw many visitors throughout the year.
Are there family friendly vacation rentals in Clearwater?
Clearwater has a variety of family-friendly stays, particularly in the beach area and residential neighborhoods close to parks or playgrounds. Many hosts provide amenities for children, such as cribs or board games.
When is the best time to visit Clearwater?
Milder temperatures and reduced rainfall in late winter and spring are often recommended for comfortable outdoor activities. This season also brings popular festivals and community events.
Quick stats about holiday rentals in Clearwater

Total holiday rentals
Explore 3,220 holiday rentals in Clearwater

Nightly prices starting at
Clearwater holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 140,660 verified reviews to help you choose

Family-friendly holiday rentals
1,780 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,100 rentals that welcome pets

Holiday rentals with a pool
1,980 properties feature pools

Rentals with dedicated workspaces
1,770 properties have a dedicated workspace

Wifi availability
3,180 of Clearwater holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Beachfront and Gym across Clearwater rentals

4.8 Average rating
Clearwater stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Clearwater’s top spots include Clearwater Marine Aquarium, Pier 60 and Countryside 12
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