Vacation rentals with a pool in Upham Beach Park

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Upham Beach Park

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

The expansive saltwater pool is enclosed by a screen, presenting a clear view of the inviting water. Comfortable lounge chairs are arranged around the pool, and a cozy seating area is visible in the background, providing options for relaxation under the blue sky.

Home in St. Petersburg

4.96 out of 5 average rating, 177 reviews

Fabulous 5BR/3BA home HUGE POOL & Poolside Cabana

This 5 BR/3Bath home sleeps 16. Let's start with the MASSIVE saltwater pool or did we mention the cute poolside cabana and the fire pit, grill and outdoor sitting lounge?! This home is in a SUPER location just 5 minute drive to the beaches & 20 mins to downtown! This home has a beautiful large kitchen, coffee bar and room to spread out with many areas to enjoy. Optional heated pool for add'l cost. Check my Airbnb profile for all 17 of our homes-each one is unique and beautiful in their own way!

Guest favorite

A cocktail pool is seen surrounded by a paved patio, featuring palm trees and tropical landscaping. Comfortable lounge chairs are positioned nearby, and a large umbrella provides shade. The serene water reflects the clear blue sky, contributing to a relaxing outdoor atmosphere.

Home in St. Petersburg

4.99 out of 5 average rating, 68 reviews

Remodeled pool cottage, just minutes from beaches

Relax by our cocktail pool in this recently remodeled guest cottage that is just minutes from the Sun Coast beaches. You will find our cottage is fully equipped and has everything you'll need for a quick getaway or an extended stay. The back door opens up to the patio and the lush, tropically landscaped backyard pool area. 5-minute drive to St Pete Beach, 7 to Treasure Island. Uber, Lyft or ride the SunRunner shuttle, and forget about the hassle and expense of beach parking. We are pet-friendly!

Guest favorite

An aerial view showcases a bright, spacious outdoor pool area surrounded by palm trees and lounge chairs. A well-maintained brick patio leads to the private pool, and the home with a large balcony overlooks this inviting space.

Home in Indian Rocks Beach

4.94 out of 5 average rating, 71 reviews

4Bdm Waterfront Home w/ Heated Pool, Walk to Beach

This 2-storey waterfront home is bright, open, and thoughtfully designed for a smooth and comfortable stay. Enjoy a large heated pool, well-equipped amenities, and attentive management. Experience the best of both poolside relaxation and beachside living—without the resort price tag. *Enjoy waterfront relaxation with a private dock *Heated pool & sun loungers *Private patio & deck with lots of seating *BBQ, SUP, kayaks *Rec room, laundry, parking *Fully equipped kitchen *6 min walk to beach

Top guest favorite

Home in Largo

4.98 out of 5 average rating, 114 reviews

Sunny Family Paradise, Heated Pool, Hot Tub & King

Discover your ideal getaway, complete with all your dreams come true! Located just minutes from stunning beaches & conveniences, this fantastic home offers endless fun! From a heated pool, hot tub, and 2 person hammock, to a fire pit, BBQ, and a fully-equipped kitchen for your delight! Your family will be close to everything when you stay at this centrally-located home. 1 min to Largo Tennis Courts, Olympic size pool, baseball 8 min to Independence Square 5 min to beach 4 min to laundromat

Superhost

A spacious pool area is enclosed by a screened setting, illuminated by gentle lighting that casts a soft glow on the water. Lounge chairs frame the pool, with a blue umbrella positioned nearby. Tropical plants can be seen beyond the enclosure, providing a serene backdrop.

Home in Tampa

4.83 out of 5 average rating, 115 reviews

7Beds/Pool/Grill/Billiards/Tampa/ Near Airport

This Ranch style home is in South Tampa's Beach Park community and features a large private backyard with pool. The single level home has 2928 sqft. of living space with an open floor concept that was recently renovated and equipped with all the modern amenities including hardwood flooring, granite countertops, recess lighting and more. Additional features of the home include newly installed privacy fence, outdoor kitchen, large screened pool enclosure Heated pools additional $25 per night

Guest favorite

A balcony view features a decorative string of shells and a sign reading 'The Beach.' In the background, well-maintained landscaping and a sparkling swimming pool are visible, with a two-story condo complex providing a pleasant backdrop under a clear blue sky.

Condo in Clearwater

4.94 out of 5 average rating, 116 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

For your best vacation, welcome to stay in our newly renovated and tastefully decorated condo for having a relaxed vacation ! Family with kids, young retired or just couples who want to spend romantic moments, everybody is welcome.The condo is located in a beautiful gated community, 10 min. by car from Clearwater Beach, voted # 1 beach in U.S. in 2013 and 2018. You can enjoy a large, beautiful heated swimming pool with salt water, a barbecue area, fitness center and an elegant clubhouse.

Guest favorite

A private heated pool is surrounded by a spacious deck featuring lounge chairs and an umbrella-shaded dining area. Lush greenery and decorative plants enhance the outdoor space, creating a relaxing spot for leisure and enjoyment.

Home in Clearwater

4.88 out of 5 average rating, 173 reviews

Poolside Bliss in Clearwater! Heated-pool/Spa

HEATED POOL FREE OF CHARGE Your vacation spot grants you exclusive use of a fully updated 3 bedroom and 2 bathroom home with a private pool! With 3 bedrooms, 7 beds, that sleeps 12 comfortably can accommodate up to 14. This home has an amazing spacious backyard for family gatherings and overall enjoyment of the outdoor spaces.Located 8 miles from the world famous Clearwater beach, it is in a prime location with many events happening nearby.Safely situated in a quiet desirable neighborhoods

Guest favorite

A screened-in outdoor area features a heated swimming pool, surrounded by paver stones. Two lounge chairs are positioned nearby, and colorful floaties are visible in the water. The scene is framed by trees and a lawn in the background, with sunlight filtering through.

Home in St. Petersburg

4.91 out of 5 average rating, 146 reviews

Heated Pool and hot tub luxury vacation house

Spend your vacation in luxury! The hot tub and heated swimming pool are perfect for a family vacation or a couples' retreat. In winter we keep the pool temperature at 85 degrees. Enjoy the stylish furniture, a huge luxurious master suite with a large walk-in closet and work desk, a fully equipped kitchen and all the extras you would expect at the resorts. The living room features a 75’ TV! Short drive to Madeira Beach and Treasure Island. Small parties are allowed. A lot of parking space.

Superhost

A heated pool invites guests to relax, surrounded by lush palm trees and vibrant landscaping. Comfortable lounge chairs sit by the water's edge, providing a suitable space for sunbathing. A gentle waterfall feature adds to the tranquil environment of the courtyard area.

Apartment in Clearwater

4.82 out of 5 average rating, 107 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

Superhost

Home in Seminole

4.88 out of 5 average rating, 143 reviews

Huge & Heated Pool Home 5 Minutes Away from Beach!

5⭐⭐⭐⭐⭐ Service & Accommodations This house is perfect for a relaxing vacation or a friend and family get-together. Perfect location 1 mile away from stunning Golf Coast beaches, including Madeira Beach, Indian Rocks, St Pete Beach, Clearwater Beach, and others. Features a heated pool all year long, billiards table, ping pong table and more! Please inquire about any questions whatsoever, and we will respond to you; we are available 24/7!

Top guest favorite

Home in Seminole

5 out of 5 average rating, 130 reviews

WOW! FREEHeated Pool& Hot Tub! 3BD/2BA 2 KING beds

Are you ready for a stylish and perfectly renovated home with a HUGE AMAZING FREE HEATED POOL and HOT TUB to escape to? Then look no further! Welcome to YOUR little slice of heaven- MASSIVE 13x 30 foot free heated pool and NICE HOT TUB ! Home is a super fast 5 min drive to the closest gulf beach. Nice fenced in yard. Pool heated oct15-april 15 at no extra fee! SUPER FAST WIFI 576mbps verified by Airbnb

Superhost

A serene pool area features lounge chairs arranged around the water, with palm trees swaying gently nearby. The backdrop displays a calm body of water, reflecting soft evening hues of blue and pink as the day transitions to night.

Condo in St. Petersburg

4.85 out of 5 average rating, 454 reviews

Waterfront condo on top floor @ Boca Ciega Resort

Great view of water. Especially beautiful sunsets! Top floor end unit for privacy. Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking the intercoastal or stay indoors and enjoy puzzles and games.