Holiday rentals in Clearwater

4.97 out of 5 average rating, 134 reviews

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.

4.91 out of 5 average rating, 324 reviews

A bright studio space features a cozy seating area with a soft blue love seat and a spacious bed adorned with white linens. Natural light filters through sheer curtains, illuminating the wood furnishings and decorative accents throughout the room.

Guest suite in Largo

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

A spacious heated pool is surrounded by palm trees, loungers, and a decorative island. The pool area features sunlit tiles, offering a refreshing escape. Nearby, a covered seating area with tables adds to the inviting atmosphere of the community.

4.89 out of 5 average rating, 83 reviews

Clearwater Vacation Rental Condo/Heated Pool

Enjoy my modern Super Clean Vacation Rental minutes from Clearwater Beach. 1st floor unit. NEW COMFORTABLE KING BED, new Fridge, new washer added 2024! Enjoy the beautiful huge Heated Pool! This condo has it all: close to beaches, shopping, restaurants, entertainment and just minutes to the white sands of Clearwater beach. A fully stocked kitchen, washer, dryer, linens, towels, beach towels, blow dryer, iron and your very own private screened in balcony. Fast WIFI, 130 channels, Netflix!

4.83 out of 5 average rating, 283 reviews

Flat in Largo

Cozy Largo Studio

Fantastic studio consisting of a comfortable queen bed, and small kitchenette, perfect for a long term stay or weekend get away. Parking on premises. Unit was newly renovated and is impeccably kept. Minutes away from popular Indian Rocks beach / Belleair beach and clear water beach. Easy hassle free check in. (This is a one room studio with 1 queen bed as shown) this is a private apartment with its own front door. Not a shared space. Close to the Largo hospital, medical students welcome

A modern kitchen is presented with stylish white cabinetry and a spacious concrete countertop. Two pendant lights hang above the bar seating, which features four black chairs. Stainless steel appliances, including a refrigerator and microwave, are visible, providing a well-equipped cooking space.

5 out of 5 average rating, 55 reviews

Wonderful Condo at Avalon - Fully Renovated

Ground Floor Completely RENOVATED!!! Amazing & Very cozy and it has a a 60” Fireplace. 1 king size bed and a queen pullout couch new style, 1 bathroom with the best water pressure including a rain shower and a hand held unit. This unit is very well equipped with everything you need and have at your home. The condo is great for a couple’s getaway or a nice family vacation. YOUR HOME AWAY FROM HOME!!! Steps to the POOL, beach chairs, Floaties, wagon, cooler, etc. The Beach is a 10 minutes!!

4.98 out of 5 average rating, 47 reviews

Lush landscaping surrounds a charming pathway leading to a white cottage. Vibrant green plants and colorful foliage are prominently featured. The patio is bordered by well-maintained mulch and manicured grass, creating an inviting outdoor space for relaxation.

Home in Clearwater

Mango Tree Cottage: bike trail

Have fun as a couple or with your family at this private luxury 1 bedroom house called the Mango Tree cottage, named after the large mango tree that sits beside it. This 1 bedroom spacious cottage has a Queen size bed, a sleeper sofa, and a private patio. Your private patio has a lounge area and child’s slide. Access to full size washer dryer upon request. Your cottage even includes 2 bicycles with direct access to the Pinellas trail that will take you downtown Dunedin or downtown Clearwater

A covered patio features four comfortable wicker chairs surrounding a glass-top table. Large windows provide views of palm trees and the sunset over the water, creating a serene outdoor space for relaxation.

4.94 out of 5 average rating, 82 reviews

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

Relax in this renovated waterfront apartment. Unwind after your day at the beach on the patio overlooking the sun setting over the water. This fresh space has everything you need for your stay; a full kitchen stocked with cooking supplies, two full bedrooms & bathrooms, a large living area with ocean views to name a few highlights. Only 5 miles to the #1 rated Clearwater Beach, 1.3 miles to the fun Downtown Dunedin, a block to the Pinellas Trail, & 1 mile to the Blue Jay’s stadium!

Superhost

A modern kitchen features an expansive marble countertop with bar seating. Two pendant lights hang above, illuminating the space. Stainless steel appliances are seamlessly integrated, and a sliding glass door opens to a small balcony with outdoor seating for two.

4.83 out of 5 average rating, 46 reviews

Avalon Sun-kissed Boutique: Luxury-free parking

Welcome! Impeccably maintained and updated one bedroom/ one bath (one king-size bed in the bedroom and in the living room the sofa easily transforms into a queen bed) this condo is a gem! Free parking and a beautiful pool for the resort-style living at its best! Clearwater Beach's famous Pier 60 is only 3 miles away, with beautiful natural Parks, an attractive Marine Aquarium, and lots of activities at your fingertips for exciting moments and unforgettable memories. And more...

A spacious bedroom features a plush king bed with a light-colored blanket and two dark nightstands on either side. Vertical windows offer natural light, while neutral gray walls and wood flooring create a calm atmosphere.

4.94 out of 5 average rating, 99 reviews

Relaxing beach gateway

Kick back and relax in this calm, stylish space.Only 5 miles from Clearwater beach! Newly renovated spacious studio with brand new bathroom and kitchenette! Spacious studio featuring 1 king bed, a fully equipped kitchenette , free 1 parking spot, high speed internet, flat screen TV. Quiet area located 5 min away from downtown Clearwater and steps away from beautiful park. There is also a dog park 5 minutes away. No smoking No parties Pets allowed 2 parking spot available

4.88 out of 5 average rating, 83 reviews

Renovated Retreat

Welcome to our cozy unit! Minutes away from Clearwater Beach where you'll have easy access to all the attractions and activities that the area has to offer. The unit is fully equipped with all the amenities you need for a comfortable and relaxing stay, including a fully stocked kitchen and laundry within the unit, an inviting living room, spacious bedroom and a modern bathroom. We look forward to welcoming you to our unit and helping you have a wonderful stay in Clearwater!

Guest suite in Clearwater

A peaceful outdoor area is surrounded by lush greenery, featuring palm trees and vibrant plants. A simple table and chairs are positioned beneath a canopy, providing a shaded space for relaxation. A whimsical flamingo decoration adds a playful touch to the serene environment.

5 out of 5 average rating, 58 reviews

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 area. Perfect for solo 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!

A modern kitchen is showcased with stainless steel appliances and a central island featuring bar seating. Sleek cabinetry and a bright light fixture enhance the space. Natural light fills the room, emphasizing the clean lines and functional design.

4.97 out of 5 average rating, 115 reviews

Clearwater Retreat • Gated Community + Heated Pool

✨ Welcome to your Cozy Clearwater Retreat! This modern 1-bedroom condo in The Avalon gated community offers comfort and convenience just minutes from Clearwater Beach. Enjoy vaulted ceilings, an open layout, in-unit laundry, fast WiFi, and a screened patio. Guests love the clean space, safe location, and the resort-style pool just steps away—perfect for couples, solo travelers, or small families.

Popular amenities for Clearwater holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Clearwater

4.98 out of 5 average rating, 304 reviews

A cozy living area is highlighted by soft green walls and ample natural light from the windows. Two comfortable armchairs and a sofa surround a central coffee table on a decorative rug. A television is positioned on a wooden TV stand, with framed artwork adorning the walls.

Private room in Dunedin

Locklie Lodge, Near DT/Water/Blue Jays/Tai Chi

4.98 out of 5 average rating, 81 reviews

A spacious living area features a large sectional sofa facing a coffee table with a woven storage basket. Light tiled floors are complemented by a soft area rug. A ceiling fan is visible above, and an open layout leads to the kitchen area in the background.

Private room in Seminole

Beach Room

4.98 out of 5 average rating, 99 reviews

Private Bedroom/Bath Near Gulf Beaches & Airports

4.95 out of 5 average rating, 264 reviews

Private room in Largo

Fully Equipped Room with in-room private Bathroom

4.89 out of 5 average rating, 205 reviews

Mint bedroom for one guest, 5 miles to CW beach

Hotel room in Clearwater Beach

A light, modern bedroom features a king-size bed with neatly arranged linens. Two bedside lamps illuminate the space, complemented by a wooden nightstand. A sliding door leads to a vanity area, while a large mirror reflects the room's openness.

4.99 out of 5 average rating, 99 reviews

Ivory Sands Beach Suites - Standard King

5 out of 5 average rating, 8 reviews

A Place Like Home

The master bedroom is equipped with a spacious bed adorned with a tropical-themed coverlet. A ceiling fan circulates air in the room, and a small TV is positioned on a stand. Natural light filters through the window, complemented by soft curtains. Decorative artwork enhances the walls.