Vacation rentals with a pool in Clearwater Beach

4.93 out of 5 average rating, 103 reviews

Home in Tampa

Cozy Tampa Home with Large Heated Pool

“No Cleaning Fee, No Chores” Your family will be close to everything when you stay at this centrally-located home. This home is located 5-10 mins from shopping centers, restaurants, gyms, pet and child daycares, community sport courts, local parks and hospitals. 20-30 mins from Bush Gardens, Downtown, ZooTampa, Tampa Airport, Cruise Port, Ben T Davis Beach, Raymond James Stadium, Hard Rock Casino, Hillsborough State Park and more. Only 1hr 30min from Disney, Universal, Sea World, Lego Park

5 out of 5 average rating, 103 reviews

Home in Palm Harbor

Coastal Escape: heated saltwater pool & beaches

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

5 out of 5 average rating, 104 reviews

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

4.84 out of 5 average rating, 168 reviews

Home in Treasure Island

Eiko Beach House 4BR/3BA Heatd Pool*Hot Tub* Pets

BEACHFRONT HOUSE Private Heated Pool & Spa, Pets OK *** Photos updated Jan 26th 2025 Enjoy amazing sunsets & white sandy beaches from this unique property. About 1/4 acre, beach front property directly on the Gulf of Mexico. Located on a quiet street in Treasure Island, just a few blocks to John's Pass shops. ENJOY great family times, never ending views of sunsets, boating, dolphins, sea birds. Great location walk to John's Pass for great shopping, restaurants, boat rentals, fishing trips.

4.97 out of 5 average rating, 372 reviews

Guest suite in Largo

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee, tea and biscuits. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Apartment in Clearwater Beach

4.9 out of 5 average rating, 135 reviews

Renovated 2025 - Retro Beach Oasis with Color Pop

Book with confidence—our property is in great shape and ready to host your Clearwater Beach getaway! -No hidden fees -No chores Just a breezy, beachy stay with: -2-minute walk to the beach -Beach Chairs -Free parking -Heated pool -Cold AC -Easy self check-in -Pet friendly (One Pet max -$150 fee) We provide essentials (linens, towels, toilet paper, soap etc.) to get you started. For longer stays, we recommend buying additional supplies. 📍648 Poinsettia Ave, Clearwater Beach, FL 33767

4.95 out of 5 average rating, 303 reviews

Condo in Tampa

Modern Waterfront Condo - Captivating Sunset Views

This waterfront one bedroom condo will be your perfect place to relax and make new beautiful memories whether is for holiday or business. It has a fully equipped kitchen. Laundry and dryers are coin operated located at third floor. Guests are allowed to use resort’s common areas like heated pool, fire pit bar/ restaurant. Located near Tampa airport (TPA). Within walking distance of public beach restaurants, and Courtney Campbell trail. Resort doesn't have access to the beach.

4.93 out of 5 average rating, 161 reviews

Home in Largo

Heated Pool Tropical Home 6min drive to the Beach

‣ Heated Pool! 💦 ‣ 6 min drive to an amazing beach! 🏝️ (Indian Rocks, free parking) ‣ 3 BR/2 BA for up to 6 guests ‣ 1 king, 1 queen and 2 twin beds + optional rollout bed 🛏️ ‣ Fun decor, perfect for bday or bachelorette parties! 🎉 ‣ Yoga mats! 🧘‍♀️ ‣ Piano! 🎹 ‣ Board Games! 🎲 ‣ Work station 💻 ‣ Modern Amenities 😎 ‣ Walking distance to Largo golf course, gym and tennis! 🏌️‍♀️ ‣ 5-star customer service 🤝 Long-term stays are welcome! Please reach out for a quote.

Townhouse in Clearwater Beach

4.99 out of 5 average rating, 110 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.

4.83 out of 5 average rating, 170 reviews

Condo in Clearwater

Lovely condo close to Clearwater Beach

Modern and cozy one-bedroom condo 10 min away from gorgeous Clearwater Beach. It’s comfortable, high-quality, a quiet corner of the community, very clean. It has nice and comfortable furniture, fine sheets, blankets, towels, etc. Spacious fully equipped kitchen and big shower, king-size bed, sleeping sofa & relaxing patio. Beach towels, chairs, umbrella, cooler. TVs in the living room and bedroom, Full cable, ROKU. Heated pool, gated community, 24h gym. Enjoy!

5 out of 5 average rating, 141 reviews

Home in Oldsmar

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Superhost

Apartment in Clearwater Beach

4.74 out of 5 average rating, 404 reviews

Surf n Sand Studio by the Water 1

Our goal is to preserve the old Florida and to offer you the opportunity to experience a stay at a vintage themed motel. Our Airbnbs are all unique. Some include neon signs, some the original colorful subway tiles, and others terrazzo floors. You will be staying at the exact Airbnb as pictured on the listing. We seek to keep the properties original and authentic by implementing repairs instead of replacements.

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Popular amenities for Clearwater Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 136 reviews

Home in Largo

Palm Oasis | Heated Pool | Near Beaches

SaralynRating, 5 stars2 days ago

Highly recommend! The house was just as advertised and better! The backyard is perfect for families. It’s safe, enclosed, and private. Not far from the beach. Would absolutely come back! We loved it.

4.88 out of 5 average rating, 168 reviews

Home in Seminole

*POOL* Bar, Hottub, Central location

DevynnRating, 5 stars3 weeks ago

House was super cute. The hosts thought of everything and had everything labeled as well as a guide book. Everything was clean. The only thing I would say was inconvenient was that we had to clean the pool frequently because of the foliage. A pool guy was supposed to come but we never saw anyone come clean the pool. That’s just a minor thing though and overall we loved our stay and would stay again!

4.91 out of 5 average rating, 114 reviews

Family Fun! Heated Pool/Arcade/Foosball + 2 Kings

KathyRating, 5 stars2 weeks ago

We were in Clearwater to celebrate my nephew’s high school graduation. Several family members came down and we were only 10 minutes from my brother’s home. We all had our own rooms with a central area to hang out. It was absolutely perfect!

4.94 out of 5 average rating, 111 reviews

Home in Apollo Beach

Apollo Beach Waterfront Amazing PoolOasis w kayaks

DavidRating, 5 stars1 week ago

This was the perfect place for a nice, peaceful long weekend. The house was perfect. Spacious and extremely clean, the pool was perfect and a nice was to relax after a day of outside activities. Love the tv on the back porch. Our last day we fished off the dock then grilled and hung out in the pool while watching a movie. It was so relaxing. Fishing was good as long as you had an outgoing on incoming tide. Caught a variety including trout. Publix and everything else you need is literally a couple miles away, but you are still in a very quiet neighborhood. The hosts were amazing. I’ve never had host respond as quick as these hosts did. They weee very helpful. The first pan is to stay here again and this time bring a boat with us. I can’t think of one negative thing to say. Everything was perfect!!

4.99 out of 5 average rating, 301 reviews

Home in Seminole

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

RobRating, 5 stars1 week ago

The house is beautiful and comfortable with a great pool, hot tub, and enormous bathtub. everything was clean. All the appliances were modern and clean, and the house left a few personal touches like a bottle of wine, you name on the welcome board, and a card welcoming you. I would stay again the next time I'm in the area.

5 out of 5 average rating, 112 reviews

FL Gem! XL-Pool | Pickleball | B-Ball & More!

BrandonRating, 5 stars1 week ago

Thoroughly enjoyed our wknd getaway stay. This place is the real deal and 100% as advertised. Tamela was a very responsive host and allowed for a flexible check in process. The location is perfect halfway between Clearwater beach and downtown Tampa.

4.92 out of 5 average rating, 98 reviews

Home in Largo

Swim-Out Bedroom, Waterfall pool! The Peace Place

Kaitlin BetkaRating, 5 stars1 week ago

The host was super accommodating and the place was clean and beautiful!

4.95 out of 5 average rating, 125 reviews

3bd 2ba House• Heated POOL•Clearwater BEACH 5miles

KarielysRating, 5 stars1 week ago

Natalia was very friendly and responsive. Inquired about the home before booking and she answered all questions. She made the check-in and check out a breeze. Home was very clean and well-kept with more amenities than expected. The backyard was gorgeous and the pool was great. Loved the home, would rent again in the future!

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Condo rentals with a pool

4.93 out of 5 average rating, 136 reviews

Condo in Indian Shores

"Jewel At The Shores" Gulf Front, sleeps 5

DerekRating, 5 stars3 weeks ago

Excellent location! Everything you need is in the condo. Hope to come back soon!

4.99 out of 5 average rating, 104 reviews

Condo in Clearwater

Seasalt Breeze private unit No cleaning fee

NicoleRating, 5 stars3 days ago

Amazing! Enjoyed the apartment along with the pool! Great location and loved the recommendations

Condo in Clearwater Beach

4.87 out of 5 average rating, 144 reviews

Beach KING Bedroom Sleeps 4-2 FIREplaces FREE PARK

KarlyRating, 5 stars1 week ago

Great location within walking distance to the beach and restaurants. Easy check-in and communication. Will definitely stay again!

Condo in Clearwater Beach

4.99 out of 5 average rating, 110 reviews

Dock of the Bay, Coastal Elegance | Walk to Beach!

JohnRating, 5 stars4 weeks ago

Perfect! Beautiful condo, fully equipped with everything you could possibly require. 5 minute walk to the stunning Clearwater Beach. Great hosts, going over and above with what they provided: Beach Towels, Beach Chairs/Parasol. Would love to return some day. Would highly recommend to anybody.

4.95 out of 5 average rating, 116 reviews

Condo in Indian Shores

Tropical Beachfront Penthouse-Beach Cottages II

StaceyRating, 5 stars3 weeks ago

We have stayed at this condo 5 times. Each time it is a perfect experience. When I read a previous review from a very unsatisfied renter, I was very confused as this place is not only beautiful it is very convenient for getting down to the pool and beach. Elevator and a few steps to either. There is continuous remodeling going on from the past hurricane damage. But it did not bother us at all. We can’t wait for next May to come around.

4.93 out of 5 average rating, 120 reviews

Condo in Clearwater

POOL VIEW IN A MODERN CONDO - Feel at Home

CassandraRating, 5 stars4 weeks ago

We loved our stay! The hosts were great at communicating with us. Very clear instructions. Place was just like the photos. Very enjoyable stay!

4.99 out of 5 average rating, 188 reviews

Condo in Treasure Island

Spectacular beach to bay views from this resort.

LaraRating, 5 stars2 weeks ago

Our stay was great! The place and location were perfect! We had absolutely everything we needed. Communication was awesome! Thanks so much!! Lara and Thomas Boulder Co