
Holiday rentals in Clearwater
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Top-rated holiday rentals in Clearwater
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Modern Private Estate | Central to Tampa & Beaches
Experience this private 1-acre, modern home designed for space, calm, and everyday comfort. Surrounded by mature oaks and palms, this serene property offers rare privacy just minutes from Tampa Airport, Clearwater Beach, Safety Harbor, St. Pete, and top attractions. Enjoy a chef’s kitchen with modern appliances, spacious living areas, and peaceful outdoor spaces with a patio, electric grill, and koi pond. Ideal for families, longer stays, & guests who value tranquility, and a thoughtful design!

Huge Spa - Quick Walk to the Beach - 2 Family Room
This beautifully decorated coastal home is just a short walk to an award-winning beach! Guests can choose between a private gated neighborhood access or a slightly closer public access. Both provide beautiful beaches and fabulous sunsets. With an open floor plan, 3 large BRs, and updated baths, this home will be perfect for one or multiple families. Relax and unwind in the gigantic SPA for 6 n the fenced in backyard! A Beach Cart and Beach Chairs are also provided! New Pickleball Courts nearby!

Fun, Funky, Fire Pit, Pool! 4 miles to Beach
Welcome to The Merry Mint! A family & pet friendly 2/1 oasis located 4mi from the #1 beach in America; Clearwater This colorful & whimsical property is just minutes from grocery, 5 star restaurants, & every convenience. Only a short drive to the beach! Or stay in & enjoy: ❇️ 24x12 Pool w/LED multicolor pool light ❇️ 34X18 Pool Deck ❇️ Loungers ❇️ 16x20 Grill Deck ❇️ Fire-Pit w/grill grate ❇️ Yard Games (regulation corn hole, jenga, connect four, etc) ❇️ BBQ Grill ❇️ string lights

Boutique Stay Near the Bay | Walk to Downtown.
Feel both transported and perfectly at home. The Barefoot House is your serene escape in the heart of Historic Old Northeast — where charm, comfort, and culture meet. Tucked away in a quiet alley, this thoughtfully designed retreat is just blocks from St. Pete’s stunning waterfront parks and a 5-minute stroll to downtown’s vibrant mix of restaurants, cafés, bars, museums, and art galleries. Guests love our blend of calming details & walkable access to everything St. Pete has to offer.

Barefoot Parrot /Walk DT & Waterfront/Sleeps 8
Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to gorgeous sunsets, shops, dining, breweries, and Pinellas Trail. Perfect for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this Dunedin favorite!

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach
You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

Lakeside Heaven Retreat in Largo - King size Bed!
Welcome to Largo, and to our fully renovated home! This spacious and centrally located retreat offers plenty of room for fun and relaxation. Just a 10-minute drive to Belleair Beach and less than 15 minutes from the award-winning Clearwater Beach. With Highland Largo Park right next door, you can step outside and immerse yourself in a peaceful natural setting, complete with scenic walking trails and a beautiful lake just steps from your front porch. We look forward to hosting you!

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.

Oak Oasis Cozy Getaway
Welcome to Oak Oasis Cozy Getaway! Whether you’re here for the sun, sand, or local eats, this comfy home is the perfect base. 5–10 minutes to Clearwater Beach Peaceful neighborhood on Oak Ave Fully equipped kitchen & fast Wi-Fi Comfortable beds & fresh linens Free street parking Ideal for couples, families, or small groups Enjoy your morning coffee on the patio, or head out to explore everything Clearwater has to offer. Your perfect Florida stay starts here!

Clearwater Studio Getaway
Welcome to Clearwater Studio Getaway! Enjoy a peaceful and centrally-located space just 15 minutes from Clearwater Beach, Downtown Clearwater, and the Tampa Bay área .Just 7 minutes from Safety Harbor and 14 minutes from Dunedin . Perfect for travelers or couples, this cozy studio features a private bathroom, comfy bed, and essential amenities. Relax after a day of sun and fun, with shops, dining, and attractions all within easy reach. Your perfect Florida stay!

Coastal Waterfront Condo 2 blocks to Beach
🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴♂️🏄♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

CWB Retreats at Baymont Lofts - Loft A
Loft A at Baymont is one block from the Sand Pearl entrance to the beach. Walk down the stairs from the spacious 2 bedroom loft, with private patio, and enjoy the local restaurants and convenient shops. Additionally, there is a queen sleeper sofa in living room. Washer and dryer in the unit is a huge perk. Full kitchen. One free, dedicated parking space per unit. 57 Baymont Street to map. New pool available at 617 Bay Esplanade you can walk to.
Popular amenities for Clearwater holiday rentals
Other great holiday rentals in Clearwater

Wonderful Condo at Avalon - Fully Renovated

Luxury Poolside Paradise

CBC 2-17A –Newly Updated Beach Front Condo!

Marie's Oasis‐4 min walk to sandy white beaches!

Modern 3BR/2B Oasis/ Patio – Sleeps 8

Beach in 90 Seconds w/ Hot Tub, Coffee Bar & Games

Welcome to the beach

Waterfront Gorgeously Updated Condo 2 Bed/2 Bah
When is the best time to visit Clearwater?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $200 SGD | $246 SGD | $290 SGD | $223 SGD | $195 SGD | $195 SGD | $196 SGD | $180 SGD | $169 SGD | $170 SGD | $183 SGD | $193 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 3,310 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 145,390 verified reviews to help you choose

Family-friendly holiday rentals
1,940 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,160 rentals that welcome pets

Holiday rentals with a pool
2,020 properties feature pools

Rentals with dedicated workspaces
1,840 properties have a dedicated workspace

Wifi availability
3,290 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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