Vacation rentals with a pool in Harbor Bluffs

A covered patio area is visible, featuring comfortable wooden chairs with blue cushions and a wooden table. The scene is framed by a screened enclosure, providing an unobstructed view of a private pool surrounded by lush tropical plants.

4.89 out of 5 average rating, 305 reviews

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

Superhost

4.82 out of 5 average rating, 127 reviews

Sunshine, Beaches & Refreshing Pool/Screen Patio

Step inside, you’re greeted by an open living area, and beautifully updated kitchen and appliances. Step outside to your private paradise! The large screened-in pool lanai beckons you to relax, lounge around, take a dip, fire up the grill and unwind in the Florida sunshine. This is where unforgettable memories are made. ☑ 5 mi to beautiful Sand Key Beach park and Clearwater Beach! ☑ 10 mi to John’s Pass Boardwalk. ☑ 9 mi to CLW/St Pete Airport & 23 mi to Tampa INTL. ☑ Sun room w/ping pong tabl

A cozy living area features two comfortable sofas adorned with cushions, centered around a round coffee table. Natural light filters through a window, illuminating a plant and decorative items on the table. Light-colored walls and a simple rug enhance the welcoming ambiance.

4.98 out of 5 average rating, 122 reviews

4BD/3BA + Pool + Hot Tub + Game Rm—5 mi to Beach!

Welcome to Coastal Comfort-- just 5 miles from the beach! • Brand New Heated Pool & Hot Tub • Game Room • Comfortable Beds for 12 • Brand New Appliances • Complimentary Coffee & Youtube TV • Water Purifier This stylish retreat offers the perfect blend of comfort and convenience, making it ideal for your next vacation. Whether you're seeking quality family time, a romantic getaway, or a fun-filled adventure with couples, friends, teams or colleagues, Coastal Comfort has everything you need!

4.91 out of 5 average rating, 204 reviews

The Oasis - Arcades - Golf & Games - HTD Pool

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

A spacious outdoor area is highlighted by a large pool surrounded by a stone patio. A dining table with multiple chairs sits beneath a wooden pergola adorned with lights. Lush palm trees and an elevated deck complete the inviting ambiance of the space.

4.93 out of 5 average rating, 186 reviews

Poolside Palms Pool & Gameroom - Mins to the beach

Poolside Palms - Just minutes from Indian Rocks Beach, Restaurants & Attractions! An indulgent getaway awaits in our fabulous 4BR/3.5BA home that features amazing indoor/outdoor entertaining space plus all the amenities to accommodate a large group of 14! Luxurious design, high-end bedrooms, comfortable and stylish furnishings, this two-level home boasts a game room & private pool and patio! Bright Livingroom, Incredible Kitchen, Elevated deck on a corner lot! Look no further - Just Book it!

An inviting pool area features a clear blue pool alongside a spacious hot tub, both surrounded by a grey stone deck. Comfortable loungers are arranged under an umbrella, offering shade. Sunlight filters through the screened enclosure, creating a bright and open atmosphere.

4.92 out of 5 average rating, 133 reviews

Heated Pool and Spa | 5 min to beach

Welcome to our home in Largo, Florida. This is a modern and comfortable place with a heated pool and spa, just minutes from Clearwater and Indian Rocks beaches. The kitchen has everything you need, and the living spaces are meant for relaxed stays with family or friends. The house has 3 bedrooms and 2 bathrooms and sleeps up to 6 guests comfortably. Whether you spend the day at the beach or by the pool, you’ll have an easy place to unwind and enjoy your time here. We hope you feel at home.

4.93 out of 5 average rating, 122 reviews

Home in Clearwater

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

A luxury heated pool is set amidst lush tropical landscaping, equipped with a tanning ledge and seating under a large umbrella. A red pool float rests on the water's surface, providing a pop of color against the clear blue water.

4.95 out of 5 average rating, 117 reviews

Insta-worthy Pool & Game Room; Luxury Florida Home

Welcome to your dream oasis 5 min away from top beaches! Swim in your, luxury HEATED pool and properly take in the Florida sun on the tanning ledge. Improve your short game on the green. Dine al fresco or in the formal dining room then share stories around the fire pit. Head inside where a game table, pool table, arcade, and bar are waiting for you. Choose from two massive sectionals for your movie night before retreating to a cozy bedroom. Book now for your perfect Florida vacation!

4.91 out of 5 average rating, 141 reviews

Villa in Largo

The Tropical Oasis, w/ Solar Heated Pool and Games

Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, mosquito-free lanai. FUN & GAMES: Enjoy Billiards (Pool Table) 🎱, Foosball, Cornhole, board games, and 3 Smart TVs 📺. PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. Essentials: 🌞 Heated Swimming Pool (Private!) 🎮 Billiard Table / Foosball Table / Cornhole / Boardgames and more! 🛏️ 4 Queen/Full Beds 🧺 Beach Amenities

4.92 out of 5 average rating, 173 reviews

Swim-Out Bedrooms, Waterfall pool, Peace Place

Unique tropical oasis complete with 2 swim out bedrooms, Tiki Hut and tiki bar! LGBTQIA + welcome! Hablo Español. Pet haven. Tropical Airbnb retreat! Our unique resort-style heated PRIVATE pool with waterfalls and dual sun-shelves, / in pool loungers, surrounded by lush landscaping, is a private oasis. 3 bedrooms, with Large 3rd bedroom with 2 queen beds At night the outdoor space comes alive with pool and landscape lighting! You wont want to leave the house!

4.96 out of 5 average rating, 182 reviews

10 Min to Beach | Heated Pool, Hot Tub, Arcades

Create unforgettable memories at this fun-filled family retreat just 10 minutes from the beach! Spend your days swimming in the heated pool, relaxing in the hot tub, grilling on the BBQ, and gathering around the fire pit under the stars & string lights. Challenge the family to arcade games, axe throwing, soccer game, giant 4 in a Row, giant X & O, and more. Close to beaches, shopping, restaurants, and attractions, it's the perfect Florida getaway.

Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

4.97 out of 5 average rating, 234 reviews

Popular amenities for Harbor Bluffs rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 237 reviews

Home in Clearwater

Specious home W/ Heated Pool ! ! ! Great Location.

4.92 out of 5 average rating, 143 reviews

The backyard features an inground pool surrounded by a smooth deck, with lounge chairs positioned beside it. Lush greenery and palm trees are seen throughout the space, enhancing the outdoor living area. A covered pergola provides shade, and a grassy area is included for relaxation.

Home in Belleair Bluffs

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach

A bright living room features a combination of plush furniture, including a gray couch and blue armchairs. A low coffee table is adorned with decorative items, including a flower vase and a lit candle, while a large window allows natural light to brighten the space.

4.98 out of 5 average rating, 120 reviews

Casa Flamingo - Private - Outdoor Bar+TV - Games

The inviting pool area features a heated pool with clear turquoise water, surrounded by lounge chairs and a spacious pool deck. A dining area and outdoor kitchen can be seen, with a large TV mounted on the wall, creating a welcoming space for relaxation and entertainment.

4.97 out of 5 average rating, 180 reviews

Palm Oasis | Heated Pool | Near Beaches

A heated pool area is surrounded by tropical plants and palm trees. A tiki hut provides shaded seating, and lounging chairs are positioned around the pool. A textured stone deck complements the inviting water of the pool, creating a relaxed atmosphere for guests.

4.9 out of 5 average rating, 129 reviews

Tiki House •Sleeps 10 •Walk to Beach + Heated Pool

5.0 out of 5 average rating, 12 reviews

Honeysuckle Waterfront | Heated Pool & Near Beach

A private outdoor space showcases a sparkling salt-water pool alongside a connected spa. Lush tropical plants and palm trees surround the area, offering a serene environment. The pool is framed by a laid stone patio, creating a welcoming atmosphere for relaxation and entertainment.

4.95 out of 5 average rating, 79 reviews

Tropical 4 Bed* Heated Pool* Min to the Beaches!

Superhost

Home in Indian Rocks Beach

Modern Oceanfront Hideaway

4.89 out of 5 average rating, 9 reviews

Condo rentals with a pool

4.95 out of 5 average rating, 128 reviews

A heated swimming pool is surrounded by neatly arranged loungers, with palm trees providing shade. A clear sky and vibrant sunset colors reflect on the water's surface. The pool area is enclosed by a black fence, ensuring a private and relaxing environment.

Condo in Largo

Boho Beach Condo

4.9 out of 5 average rating, 238 reviews

A bright living room features a gray couch with colorful accent pillows, positioned next to a coffee table. Large sliding glass doors open to a view of the patio. A rug with intricate designs lies on the floor, complemented by a cozy accent chair.

Condo in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

A light blue living room features two armchairs and a sectional sofa, complemented by a white coffee table at the center. Large windows with blinds allow natural light to brighten the space, while a decorative throw and small lamp add subtle accents. A rug covers the floor.

4.93 out of 5 average rating, 112 reviews

The Shack at IRB

4.72 out of 5 average rating, 548 reviews

A balcony view that captures the tranquil beach scene, featuring soft pastel hues in the sky. A round table with intricate design sits next to two woven chairs. Below, umbrellas dot the sandy beach, while gentle waves touch the shore.

Condo in Belleair Beach

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

A comfortable living area is presented with a spacious sectional sofa adorned with decorative pillows. A large flat-screen TV is mounted on a wooden accent wall, enhancing the cozy atmosphere. The open layout leads towards a bright kitchen visible in the background.

4.9 out of 5 average rating, 148 reviews

Golf Cart, 2 bed 2 Bath, Heated Pool

The inviting living space is furnished with a blue sofa, two armchairs, and a white coffee table. A starfish-patterned rug adds a nautical touch. Natural light filters through window blinds, illuminating the area. The open layout connects to the kitchen, visible in the background.

4.97 out of 5 average rating, 149 reviews

Beach Across the St | No Stairs |Parking in Front!

A vibrant water park area features colorful water slides curving overhead, with a rocky structure resembling a pirate ship in the foreground. The clear blue water in the pool invites guests to enjoy a refreshing experience, framed by lush greenery and sunny skies above.

4.87 out of 5 average rating, 195 reviews

Waterfront, Harbourside, Water Park, Beach, #8819

Condo in Clearwater Beach

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

4.98 out of 5 average rating, 182 reviews

Other vacation rentals with a pool

Villa in Indian Rocks Beach

Heated Hybrid Pool~Modern Beach House~Walk 2 beach

4.93 out of 5 average rating, 160 reviews

Bungalow in Indian Shores

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

4.97 out of 5 average rating, 206 reviews

4.97 out of 5 average rating, 427 reviews

A clear blue pool is surrounded by lush greenery, including palms and other tropical plants. A red umbrella provides shade over a seating area nearby, while lounge chairs are positioned along the pool's edge, inviting relaxation in a serene outdoor setting.

Guest suite in Largo

Private Pool, Jacuzzi, Walk to Beach.

4.97 out of 5 average rating, 58 reviews

Private Pool Oasis | 4BR • Game Room • Mini Golf

Home in Indian Rocks Beach

Bougie Bungalow: Golf Cart | Pizza Oven | 1GB Wifi

4.97 out of 5 average rating, 39 reviews

4.92 out of 5 average rating, 13 reviews

Heated Pool • Games • Near Indian Rocks Beach

5.0 out of 5 average rating, 41 reviews

Home in Belleair Bluffs

Mins to Beach, Heated Pool, MiniGolf, Firepit