Holiday rentals with a pool in Sawgrass

Guesthouse in Isle of Palms

4.95 out of 5 average rating, 204 reviews

Il Rifugio waterfront retreat on the ICW by Mayo!

Our pool cabana is located in a peaceful location on the intercoastal waterway and perfect place to be close to Mayo clinic (2 miles) or get away and relax. Private building with large main sleeping/living area and private bathroom. Newly remodeled backyard and pool. Sleeps up to 5 (1 king size + 1 full + 1 twin) . 5G wifi. EV charger 2. Close to beaches (4 miles), restaurants, miles; TPC/ Sawgrass Golf ,10 miles; Saint Johns Town Center shopping 10 miles; Jacksonville Intl Airport, 25 min.

5 out of 5 average rating, 149 reviews

Home in St. Augustine

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

A sunlit backyard showcases a private heated pool surrounded by a stone patio. Comfortable lounge chairs are positioned beside the water, while lush greenery and palm trees provide shade and privacy. The pool area features a gentle curve, enhancing the inviting atmosphere.

5 out of 5 average rating, 146 reviews

*Heated Pool Home in Ponte Vedra Beach!

Ponte Vedra Beach retreat with heated Pool! (Heated at 83 degrees March, April, May, September, October) Southern Palms is newly renovated. Ideal for beach lovers, shoppers, and golfers; this single-story residence with 3 bedrooms and 2 baths offers all the home essentials, plenty of private outdoor entertainment, and a prime location near the Atlantic Ocean! Close to St. Augustine, Mayo Clinic and Sawgrass, Ponte Vedra Beach is the perfect place to get away, with everything you need close by.

4.94 out of 5 average rating, 216 reviews

The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.

Home in St. Augustine

Downtown Luxury • Gourmet Kitchen • STEPS 2 DTWN !

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

A sparkling blue pool is outlined by a clean white patio, featuring multiple lounge chairs positioned for relaxation. The single-story home is visible in the background, surrounded by lush greenery and trees, creating a serene outdoor environment.

4.91 out of 5 average rating, 149 reviews

Pool Home with Game Room in Heart of Jax Beach!

Beautiful pool home in Jax Beach! This updated and sparkling clean home is in the perfect spot for the whole family! This home is in the perfect location, minutes to the ocean, restaurants, Mayo Clinic and more! It is equipped with everything you need for your ideal coastal vacation. Your stay includes a fully stocked kitchen, pool table, ping pong table, dart board, Smart TVs, a beautiful pool with set up with lounge chairs, outdoor dining, beach chairs, beach towels, and a charcoal grill.

4.98 out of 5 average rating, 111 reviews

Home in St. Augustine

HTD Pool with Arcade, Fire Pit, and Putting Green, 1.2 miles DT

ISLE BE BACK 🌴— a brand NEW modern home! Dates fill quickly for spring & summer — save your stay now! Welcome to your ultimate St. Augustine getaway! Just 5 mins from downtown, this fun-filled retreat is perfect for families, friends, or anyone looking to relax and play. Swim in the pool, compete on the putting green, roast s'mores by the fire pit, or challenge your crew on the retro Pac-Man machine—all without leaving the house! ✔ Sleeps 8 comfortably ✔ Easy self check-in & free parking

Apartment in Ponte Vedra Beach

An aerial view of the gated Sawgrass community reveals lush landscaping and well-maintained buildings. The shimmering ocean is visible in the background, with private beach access indicated by a directional arrow. A community pool can also be seen, surrounded by palm trees and parked cars.

4.98 out of 5 average rating, 102 reviews

Light, Airy Luxury Condo with Private Beach Access

Located in the gated Sawgrass community with private beach access, this beautiful studio condo is the ideal choice for a relaxing beach vacation. The privacy and beauty of the coastline rivals any beach destination in the US. The inviting, tranquil elegance of the low country-inspired decor provides the backdrop for your best vacation yet. The vaulted ceilings of the second floor unit give a light and airy feel to the space. You will relax and unwind the moment you step through the door!

Townhouse in Ponte Vedra Beach

A spacious living area features a comfortable sectional sofa adorned with blue and white cushions. A white coffee table sits in front, accompanied by a cozy area rug. Large windows provide a view of the outdoors, while a television is mounted above a charming fireplace.

4.97 out of 5 average rating, 126 reviews

Waterfront Villa in TPC Sawgrass (2 Bedroom)

Coastal Vibes Villa is newly renovated, spacious, and has a view! Your vacation Oasis awaits! Located in beautiful TPC Sawgrass. Community pool is right across the street and you are walking distance to Sawgrass Village- home of some of Ponte Vedra’s finest restaurants and shopping. You will also enjoy the close proximity to various spas, beautiful beaches and the iconic TPC golf course. Coastal Vibes Villa is perfect for your next event, golf outing, wedding, or just a relaxing getaway.

4.97 out of 5 average rating, 110 reviews

Heated pool! Bikes, game room, & more!

Talk about relaxation, vacation vibes! Walk back from the beach to this immaculate home! Renovated with a new, heated saltwater pool! This home features 4 bedrooms, a game room, fully equipped kitchen, and spacious screened porch. You'll love the sparkling pool & lounge chairs, hammock, firepit, and outdoor BBQ area. Open up the double garage doors to feel the ocean breeze while playing in the game room. Truly a place to gather & enjoy! Less than 10 minutes from Mayo as well!

A vibrant sunset casts warm orange and pink hues across the sky, reflecting on the calm ocean waters. The beach is visible below, with gentle waves lapping at the shore. Lush green dunes frame the scene, creating a serene coastal atmosphere.

4.95 out of 5 average rating, 115 reviews

Oceanfront Oasis: Top Floor Paradise

Oceanfront Oasis is located in the heart of Jax Beach. It is the perfect oceanfront getaway with breathtaking views and direct beach access only steps away.This 5th top floor,2 bed/1bath,oceanfront condo has been completely renovated and is equipped with everything you need.Relax on the private balcony while sipping on your morning coffee as you listen to the waves.This unit is close to everything you need-coffee shops, restaurants, and shopping.Mayo Clinic is 5 minutes away.

A contemporary home sits beside a heated pool and spa, framed by elegant palm trees. Multiple lounge chairs are positioned around the pool, with plush seating options visible on the patio. Large glass doors offer an unobstructed view of the outdoor area, inviting natural light.

4.93 out of 5 average rating, 165 reviews

Paradise Palms Estate

Located off the popular, scenic Roscoe Boulevard this home sits directly on Cabbage Creek connecting to the Intracoastal water way. Enjoy a private dock, heated pool, spa, fire pit, hammock and oasis. This contemporary home is nestled on a private street with 300 foot long driveway on an acre and is less than a mile from the world renowned TPC golf course as well as exquisite dining, luxury shopping and the historic city of St. Augustine. Plan your escape today!

Cottage in Fort George Island

A white high-top chair is positioned on a deck overlooking the calm waters of the St. Johns River. Lush greenery can be seen in the foreground, while a clear blue sky stretches above, providing a serene backdrop for relaxation.

4.88 out of 5 average rating, 312 reviews

Salty Dolphin Cottage with Pool ❤

Welcome to the Salty Dolphin—where the St. Johns River meets the Intracoastal. This peaceful riverfront townhome offers stunning views, dolphin sightings from the decks and dock, and is just 3 miles from the Atlantic—perfect for fishing. You’re minutes from JAX Airport, downtown, Amelia Island, Ribault Club, and a ferry ride from Mayport. Relax, explore, or cast a line—this hidden gem puts the best of Florida’s First Coast at your doorstep.

Popular amenities for Sawgrass rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 53 reviews

Oceanfront | Pool, Pet Friendly, Large Deck!

4.89 out of 5 average rating, 239 reviews

A private swimming pool is surrounded by a spacious patio, featuring white lounge chairs and two large umbrellas for shade. Comfortable blue seating is positioned nearby, offering a relaxed outdoor gathering space. Lush greenery forms the backdrop, enhancing the tranquil setting.

Home in Isle of Palms

Private Pool Getaway • 5 min Beach • Sleeps 9

4.99 out of 5 average rating, 147 reviews

The outdoor area features a private saltwater pool with a custom spa, surrounded by lush tropical landscaping. A spacious cabana is included, with comfortable seating beneath flowing white drapes. A shaded umbrella is positioned beside the pool, enhancing the relaxation space.

Home in Vilano Beach

2023 Lux Home 4bd/3.5ba + SaltPool + HotTub + Walk2Beach

4.86 out of 5 average rating, 151 reviews

Luxury Pool House Perfect For Family Getaway!

An outdoor space features a rectangular saltwater pool surrounded by lounge chairs. Green foliage and a wooden fence provide privacy, while a shaded area includes a seating structure. The clear water of the pool reflects sunlight, inviting relaxation.

4.9 out of 5 average rating, 105 reviews

Pool & Hot Tub Home w/ Game Room! 1 Mile to Beach!

4.96 out of 5 average rating, 26 reviews

An expansive saltwater pool features both deep and shallow areas, surrounded by lush greenery. A gazebo is visible to the left, offering shade, while a well-maintained lawn extends beyond the pool. The clear blue sky reflects off the water, enhancing the tranquility of the outdoor space.

Home in Sandalwood

The Happy Place

4.93 out of 5 average rating, 177 reviews

A spacious screened-in pool area features a large blue swimming pool surrounded by patio tiles. Comfortable seating arrangements with multiple chairs and a table are visible nearby, providing a relaxed space for leisure. Natural light streams in through the screened enclosure.

Home in Vilano Beach

Heated Pool, Beach, Patio Lounge, Near Downtown

4.96 out of 5 average rating, 180 reviews

A tranquil backyard area is featured, showcasing a heated pool surrounded by lush greenery. Two black chairs are positioned on the stone patio, offering a comfortable spot for relaxation. The space is enclosed by vibrant tropical plants, enhancing the private atmosphere.

Home in Vilano Beach

Pool home oasis steps to ocean

Condo rentals with a pool

5 out of 5 average rating, 144 reviews

A vibrant sunset casts warm hues across the sky, with wispy clouds highlighted by the fading light. A palm tree stands prominently in the foreground, while a wooden boardwalk leads toward the beach and the ocean, framed by patches of greenery.

Condo in Butler Beach

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO WITH POOL

4.94 out of 5 average rating, 124 reviews

A balcony view showcases a serene pool surrounded by lush green palm trees and well-maintained grounds. Comfortable outdoor seating is positioned near a glass table, while the sky features fluffy clouds and hints of blue.

Condo in St. Augustine

Spanish Colonial Design One Bedroom Condominium

An aerial view captures the sandy beach stretching along the coastline, featuring clusters of umbrellas and beachgoers. The pier extends into the ocean, while a vibrant skyline of buildings is visible in the background, providing a scenic contrast to the blue waters.

4.92 out of 5 average rating, 106 reviews

Ocean front Beachside Bliss

The living area features a comfortable dark blue sofa accented with teal cushions. A stylish coffee table sits in front, while a television is mounted on the wall opposite. Large sliding glass doors lead to a private outdoor space, allowing natural light to fill the room.

4.85 out of 5 average rating, 143 reviews

Fun in the Sun - OCEAN FRONT!

4.93 out of 5 average rating, 108 reviews

The living room features sliding glass doors that open to a private balcony overlooking the ocean. A comfortable blue armchair by the window is complemented by light blue curtains, while natural light fills the space, creating a serene ambiance.

Condo in Crescent Beach

Hideaway at Crescent Breach - St. Augustine

Condo in St. Augustine Beach

The living area features comfortable seating, including a soft blue sofa and an armchair, arranged around a white coffee table. Light-colored décor and subtle greenery create a relaxed ambiance. The space is illuminated by a contemporary chandelier, with a view of the kitchen and dining area in the background.

4.95 out of 5 average rating, 175 reviews

Newly renovated! Steps to BEACH & POOL!

4.95 out of 5 average rating, 198 reviews

A spacious bedroom is equipped with a large bed adorned with plush, blue pillows. A sliding glass door opens to a private balcony offering a scenic view. A small seating area with two chairs is visible outside. A flat-screen TV is positioned on a dresser.

Condo in Crescent Beach

After Dune Delight, BEACH FRONT w/Fishing Pier

An aerial view showcases the expansive sandy beach bordered by gentle waves and the ocean. Towering buildings are visible in the background, with the highlighted condo location marked in red. Sunbathers and walkers can be seen along the shoreline, emphasizing the beach's inviting atmosphere.

4.97 out of 5 average rating, 222 reviews

Beachcomber Oceanfront 180* panoramic view

Other holiday rentals with a pool

4.96 out of 5 average rating, 48 reviews

Home in Jacksonville

XL family home, Pool, Pool table, Private 1 acre.

Condo in Ponte Vedra Beach

A spacious living area features a light-colored couch and a coordinating armchair, arranged around a wooden coffee table. Natural light floods in from large glass doors overlooking the outdoor landscape. Decorative elements include a tropical wall art piece and a stately lamp with an organic design.

4.94 out of 5 average rating, 64 reviews

616 Surf Villas, Oceanfront, BAM Vacation Rentals

4.99 out of 5 average rating, 92 reviews

A modern kitchen features sleek white cabinetry and a spacious island with seating for five. Black pendant lights hang above the island, while a wine rack is mounted on the wall, blending functionality and style. Natural light fills the room through large windows.

Home in Isle of Palms

Lux Pool Home Close to Mayo & Jacksonville beach!

Guesthouse in Ponte Vedra Beach

A spacious swimming pool is enclosed by a screened structure, offering privacy and shade. Two umbrellas provide shelter over lounge chairs for relaxation. The backdrop features a porch with seating, surrounded by lush greenery that enhances the serene atmosphere.

4.9 out of 5 average rating, 94 reviews

Palm Valley Pool House

A spacious outdoor area is featured with a modern pool, surrounded by lush landscaping and palm trees. Comfortable lounge chairs and an umbrella provide shaded seating, while a barbecue grill is positioned beside a wooden deck, ideal for relaxed gatherings.

4.96 out of 5 average rating, 57 reviews

Brand NEW Jax Beach Bungalow

Superhost

4.84 out of 5 average rating, 89 reviews

Seaside Paradise - Pool! Spa! Game Room! 12 Beds!

4.92 out of 5 average rating, 84 reviews

The exterior of a raised, single-story home is displayed, featuring a spacious deck with potted plants and outdoor seating. Sturdy wooden railings provide a welcoming touch. Surrounding greenery and a concrete area enhance the natural setting, offering a serene environment for relaxation.

Cabin in Middleburg

Rest, relax, revive-lovely 1 bedroom cabin