Holiday rentals with a pool in Tarpon Springs

4.97 out of 5 average rating, 136 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.

4.96 out of 5 average rating, 143 reviews

The screened outdoor lanai features a heated pool with steps leading into the water. Comfortable seating options are present around the pool area, complemented by a shaded dining space nearby. Lush greenery surrounds the outdoor space, enhancing the relaxing environment.

Home in Tarpon Springs

Heated Pool, 5 minutes to Beach!

Welcome to Tarpon House Florida, located in the exclusive and historic Tarpon Springs. Our home is a tropical oasis. Perfect for families, couples, and anyone who needs the space to spend time together or enjoy some privacy for enjoyment and relaxation. 10% discount for Military, First Responders, Teachers, friends and family - book & message me, I'll apply the discount, that's it! Completely renovated with all new furniture. Link to 3D Tour of the house is in my guidebook (under my profile)

4.99 out of 5 average rating, 263 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool/Coffee Bar/Fully Stocked

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

4.94 out of 5 average rating, 116 reviews

Two black rocking chairs with Buccaneers branding are positioned on a light-colored deck. Lush green grass and palm trees frame the view, with a path leading to a screened-in patio visible in the background under a bright blue sky.

Home in Port Richey

Gulf Harbors Vacation Oasis

This lovely Gulf Harbors home with open floor plan & in-ground heated pool is the perfect getaway! Home on canal that leads directly to the Gulf in minutes-amazing view & quiet, safe neighborhood! Perfect home base for shopping, restaurants, kayaking, exploring, & especially Scalloping in Pasco county! This region includes all state waters south of the Hernando – Pasco county line & north of the Anclote Key Lighthouse in northern Pinellas County,& includes all waters of the Anclote River.

Guest suite in Tarpon Springs

A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.

4.96 out of 5 average rating, 139 reviews

Private pool suite in heart of Tarpon Springs!

Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

4.91 out of 5 average rating, 128 reviews

A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.

Home in Forest Hills

Heated Pool • Near Tarpon & Gulf Beaches 5 mi

🌴 Heated private pool oasis (Nov–Mar) 5 mi to Tarpon Springs—ideal to recharge. 🏡 Private patio for BBQ and outdoor time in a quiet area for great sleep. Perfect for families & friends: fast Wi-Fi + workspace, fully equipped kitchen, 🔑 24/7 self check-in, and 🚗 on-site parking. Easy access to Dunedin, Clearwater, Tampa, and beaches (times vary with traffic). ✨ Note: pool heat available Nov–Mar (weather permitting). ⏳ Last-minute promos active—book and lock in your dates!

4.96 out of 5 average rating, 375 reviews

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

5 out of 5 average rating, 102 reviews

A private backyard pool area is featured, showcasing a clear blue in-ground pool surrounded by lounge chairs and sunbeds with striped cushions. Lush greenery and potted plants add a tranquil touch, while a shaded umbrella stands at one end for comfort.

Guesthouse in Ozona

Private pool, steps to gulf, fishing, bike trails

Escape to your private Palm Harbor oasis! This updated studio features a cozy queen bed, sofa bed, and kitchenette, plus a sparkling in-ground pool reserved just for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or hop on the nearby Pinellas Trail for biking and exploring. Enjoy beaches just minutes away, along with amazing dining, breweries, and live music in historic downtown. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

Condo in Indian Rocks Beach

A spacious balcony is bordered by tall palm trees, offering a view of the calm Gulf of Mexico and white sand beach. The clear blue sky complements the serene ocean, creating a tranquil setting for relaxation.

4.89 out of 5 average rating, 103 reviews

Gulf-View 2BR/2BA Beach Condo!

This Indian Rocks Beach Gulf Front Hamilton House building is located directly on unique Clearwater- St.Pete white sand beach with private beach access and heated pool, washer and drier in the unit. Our 3rd floor 1100 sq. feet 2 bedroom condo #207 offers a spacious balcony bordered with palm trees with northerly nice side view of the Gulf of Mexico and white sand beach that goes on for miles. Two assigned parking spaces (one under the building and second uncovered).

4.99 out of 5 average rating, 263 reviews

A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.

Apartment in Dunedin

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

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.

4.99 out of 5 average rating, 148 reviews

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, 118 reviews

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!

Popular amenities for Tarpon Springs rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

A serene outdoor pool area is highlighted, featuring a crystal-clear solar-heated pool. Two lounge chairs are positioned alongside the pool, with lush greenery providing a natural backdrop. A stacked stone waterfall adds a tranquil touch to the secluded space.

Home in Fox Chase

4.9 out of 5 average rating, 58 reviews

Paradise in Palm Harbor l Free Heated Pool

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

4.96 out of 5 average rating, 92 reviews

Private pool, Golf Cart, Completely Renovated!

4.96 out of 5 average rating, 68 reviews

A light-filled living area features a spacious sectional sofa and a wooden table with a decorative chair. Natural light streams in through large windows with shades, illuminating the neutral color palette and coastal-inspired decor, creating a relaxed environment.

Home in Forest Hills

*NEW* Riverside Retreat w/Pool

A screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.

4.95 out of 5 average rating, 163 reviews

Tropical Getaway w/Heated Pool & King Beds

4.84 out of 5 average rating, 126 reviews

A spacious outdoor area features a heated pool surrounded by a screened enclosure. Two lounge chairs are positioned beside the pool, and a barbecue grill is visible near the edge, providing an ideal setting for relaxation and meals.

Home in Clearwater

Heated Pool | 2BD 2BA | Home near Beaches

Superhost

A private solar-heated pool is surrounded by lush greenery, creating a serene outdoor space. Two lounge chairs are positioned poolside, with a small table nearby, inviting relaxation in a peaceful atmosphere.

Home in New Port Richey

4.79 out of 5 average rating, 121 reviews

Pool Paradise - Private Solar Heated Pool

The outdoor pool area is enclosed by a screened-in patio, featuring a large private pool and a heated spa. Colorful pool floats rest on the water, while comfortable seating and a dining area are visible in the background. Natural light filters through the structure, creating a relaxed atmosphere.

5 out of 5 average rating, 39 reviews

Tropical House | Hot Tub & Pool | Near Beach +Pets

Superhost

A serene outdoor area features a heated pool surrounded by several loungers and a small table. The pool area is bordered by lush greenery, while the adjacent building showcases large windows that allow ample natural light inside.

Home in Dunedin

4.87 out of 5 average rating, 102 reviews

Downtown Dunedin B&B Casa w/ Heated Pool

Condo rentals with a pool

The entrance to the Avalon condo complex is presented, featuring a decorative fountain surrounded by lush greenery and palm trees. A welcoming sign indicates the name of the property. The building showcases a well-maintained façade under a clear blue sky.

4.88 out of 5 average rating, 112 reviews

Amazing main floor condo at Avalon

4.86 out of 5 average rating, 355 reviews

An inviting courtyard area is showcased, featuring a sparkling heated pool surrounded by lounge chairs. Lush greenery and well-maintained gardens add a natural touch, while the two-story yellow building encloses the area, creating a serene and communal atmosphere for relaxation.

Condo in Redington Beach

Royal Orleans at Redington Beach ( Studio )

4.98 out of 5 average rating, 101 reviews

Lovely Condo minutes from beach & King bed

An exterior view of a yellow condo building is depicted, featuring palm trees and shrubs. A pathway leads to a private entrance, while large windows allow ample natural light. The surrounding landscaping creates a welcoming atmosphere in the gated community.

4.96 out of 5 average rating, 136 reviews

Bright and Spacious 1Bed/1Bath condo.

4.94 out of 5 average rating, 133 reviews

The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.

Condo in Indian Shores

Tropical Beachfront Penthouse-Beach Cottages

A cozy bedroom is illuminated by natural light streaming through large windows adorned with patterned curtains. A spacious bed is dressed with floral bedding, accompanied by decorative pillows. A bedside table holds a lamp, and a framed art piece enhances the calming atmosphere, with the pool view visible outside.

4.94 out of 5 average rating, 127 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

4.98 out of 5 average rating, 149 reviews

An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.

Condo in Treasure Island

Beach, dolphin/manatee sightings, fishing, sunsets

4.96 out of 5 average rating, 161 reviews

Condo in Sunset Beach

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

Other holiday rentals with a pool

4.94 out of 5 average rating, 52 reviews

The dining area features a modern table with gold accents, surrounded by plush gray chairs. A stylish chandelier hangs above, illuminating the space. The open-concept layout offers a clear view of the adjacent kitchen and a spacious living area with a large television.

Villa in Palm Harbor

Villa Luxe~Heated Saltwater Pool~Near Beaches

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, 56 reviews

Wonderful Condo at Avalon - Fully Renovated!

4.94 out of 5 average rating, 17 reviews

Stylish NEW one bedroom condo Clearwater beach

A modern two-story home features a balanced façade with white walls and large arched windows. Lush palm trees and landscaped greenery frame the entrance, creating an inviting approach. The dual garage doors provide additional functionality, complementing the home's contemporary design.

4.98 out of 5 average rating, 66 reviews

Luxury Waterfront w/ Private Heated Pool

Condo in Independence Square

An open living area showcases large sliding glass doors with stunning ocean views. A comfortable seating arrangement features a dark leather couch and coordinating throw pillows. A modern ceiling fan hangs above, while a dining table is set with a centerpiece and blue accents.

5 out of 5 average rating, 21 reviews

Sea Side Sunsets Unit C

4.93 out of 5 average rating, 29 reviews

Heated Pool Near Beaches | Sleeps 10 & MIL Suite

4.99 out of 5 average rating, 72 reviews

A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.

Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool