Holiday rentals in Clearwater

4.94 out of 5 average rating, 17 reviews

Apartment in Sand Key

CBC 1-15E–High-End Stay, Low Seasonal Pricing!

🌴Luxury Beachfront Condo at Crescent Beach Club 15E | Spectacular Gulf Views & Resort Amenities Looking for the perfect coastal escape? Look no further than Crescent Beach Club 15E in Clearwater Beach, managed by Sandy Feet Vacation Rentals! This luxurious 2-bedroom, 2-bath condo on the 15th floor offers breathtaking Gulf of Mexico views from every room. Fully updated with modern coastal décor, this beachfront retreat provides waterfront living at its finest, featuring three private balconies!✨

4.98 out of 5 average rating, 51 reviews

Coastal 3BR Oasis | FREE Heated Pool & Fire Pit

Welcome to your Clearwater getaway in Sunny Florida - a modern, family-friendly 3BR/ 2BA home just a short drive from world famous Clearwater Beach. This inviting escape blends comfort, convenience, and style, offering the perfect base for relaxation, family fun, and exploring Florida’s Gulf Coast attractions. 🌟 Clearwater Beach – 20 min drive 🌟 Honeymoon Island State Park – 18 min drive 🌟 Tampa International Airport – 25 min drive 🌟 BayCare Ballpark (Phillies Spring Training) – 8 min drive

4.98 out of 5 average rating, 165 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

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

Apartment in Clearwater Beach

A private balcony is seen featuring two white chairs and a table, offering uninterrupted views of the Gulf of Mexico. The calming blue sky meets the horizon, enhancing the serene beachfront experience.

4.91 out of 5 average rating, 296 reviews

Beachfront in exclusive resort

This upper floor, 3-bedroom modern chic condo hotel suite offers sweeping views of the Gulf of Mexico from private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the shrimp trawlers making their way out to sea. Enjoy a cocktail while watching the sunset over the open water of the Gulf of Mexico. This suite can sleep 8, with King or Queen-size beds in each of the three bedrooms, a comfortable full-sized sofa bed in the living room & 3-1/2 bathrooms.

Guest house in Clearwater

The living area is furnished with a light-colored sofa and an ottoman, offering comfortable seating. A smart TV is mounted on the wall, and a wooden dining table is visible nearby. A ceiling fan provides airflow, with natural light filtering through a nearby window.

4.93 out of 5 average rating, 102 reviews

Adorable Vintange Style guest house-King size bed

Welcome to the beautiful city of Clearwater, and to our newly renovated Vintage Style Guest house. Conveniently located within 0.5 miles or 7 minutes walking to clearwater downtown, and 3 miles or 7 minutes driving to the famous and award winning Clearwater beach. Easy access to local restaurants, bars, stores, and parks. This comfortable guest home features unique layout with Vintage-modern decor, free WiFi, smart TV, LVT flooring and sleeps up to 4 people. It also offers one free parking.

4.92 out of 5 average rating, 62 reviews

Luxury Heated Pool Big House - Clearwater Beach

DREAM HOUSE FOR AN AMAZING GETAWAY IN CLEARWATER! 🌴✨ Only 14 minutes from the stunning Clearwater Beach, this modern escape has it all! Relax in the chic living room with exclusive furniture, a 65” Smart TV, and an electric fireplace. Enjoy 3 stylish bedrooms, 2 full bathrooms, and a large kitchen with an island for home-cooked meals. Step outside to your private oasis — a GREAT POOL, sunbeds, garden sofa, and a BBQ area perfect for family feasts. Comfort, style, and fun all in one place!

A cozy outdoor area is enhanced by a fire pit surrounded by multiple seating options. The pool glows invitingly under the evening sky, with soft lighting strung above. A sun shade protects this relaxing space, creating an ideal setting for gatherings.

4.9 out of 5 average rating, 110 reviews

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.

Townhouse in Clearwater Beach

The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.

4.99 out of 5 average rating, 132 reviews

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.

4.98 out of 5 average rating, 153 reviews

A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.

Apartment in Clearwater

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

4.99 out of 5 average rating, 119 reviews

Apartment in Clearwater

Literally: 15 steps to the Pool, GroundFloor Condo

Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!

4.93 out of 5 average rating, 168 reviews

A charming two-story building is nestled among lush greenery and vibrant flower beds. Large oak trees with hanging moss provide shade, while a welcoming staircase leads to the entrance. Outdoor seating areas are visible, enhancing the garden's tranquility.

Flat in Tarpon Springs

Cozy Carriage House at Spring Bayou

This is a beautiful large one bedroom apartment located in the heart of Tarpon Springs. The entire "2nd floor" apartment is yours to enjoy. Close to shopping, Greek village on the Anclote River , and many fine dining establishments. We are minutes from some of the most beautiful beaches in Florida. We are central to most of Florida's popular vacation attractions. You will love it.

4.88 out of 5 average rating, 65 reviews

A cozy bedroom features a queen-sized bed adorned with a colorful patterned quilt, complemented by solid-colored pillows. Nearby, two nightstands with lamps flank the bed, while a decorative floral artwork hangs above. A light wooden floor adds a warm touch to the space.

Apartment in Clearwater

Avalon At Clearwater Comfortable 1 Bedroom

The Avalon at Clearwater is gated resort-like condominium community that offers a family friendly environment with a free parking, heated swimming pool, 24/7 fitness facilities, and a luxury clubhouse with a kitchen, fireplace, and a barbecue area. It is located in the heart of Clearwater Florida and is within a walking distance to great restaurants, grocery stores.

Popular amenities for Clearwater holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Clearwater

The kitchen features a modern design with turquoise tiled backsplash and white cabinetry. Stainless steel appliances, including a microwave and oven, are present. Open shelving showcases decorative items and plants. The spacious countertop offers ample preparation space, complemented by natural light from the nearby window.

4.96 out of 5 average rating, 53 reviews

Home in Clearwater - Cozy 2BR/2BA Retreat

A dining area is presented with a white table set for six, featuring decorative plates and glasses. Modern, cushioned chairs surround the table. In the background, the kitchen is visible, with wooden cabinetry and stainless steel appliances, enhancing the space's functionality.

4.8 out of 5 average rating, 40 reviews

Villa Florentina. Pet friendly, office station.

A spacious living area features a light-colored sectional sofa surrounding a black coffee table. A large flat-screen TV is mounted on the wall, complemented by a stylish wooden console. Natural light filters through multiple wide windows, enhancing the room's airy feel.

5 out of 5 average rating, 23 reviews

Modern 3BR/2B Oasis/ Patio – Sleeps 8

Superhost

Villa in Clearwater

4.83 out of 5 average rating, 24 reviews

5BR Pool Villa | Game Room | Near Clearwater Beach

Superhost

Home in Largo

5 out of 5 average rating, 3 reviews

Largo Pool Home with Grill & Private Yard

The living space features a combination of seating options, including bright blue chairs and a vibrant yellow couch, arranged around a coffee table. A large television is mounted on a grey wall, and the adjacent dining area includes a wooden table surrounded by white chairs, with a decorative runner.

4.97 out of 5 average rating, 59 reviews

Home minutes from Clearwater Beach

Cottage in Indian Rocks Beach

A family beach house is showcased, featuring a main structure with a covered porch and large windows. Adjacent is a smaller cottage. Both buildings have a light-colored exterior and are surrounded by soft sandy ground and palm trees, highlighting the beachfront location.

4.97 out of 5 average rating, 35 reviews

Kamp Komfort Historic Family Beach House