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Holiday rentals with a pool in St. Augustine Shores

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in St. Augustine Shores

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

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Top guest favourite
The exterior of a single-story house is displayed, featuring a sloped roof and an inviting entryway. Green grass surrounds the home, complemented by mature trees and landscaped bushes. A concrete driveway leads up to the entrance, providing accessible access.
Home in St. Augustine
4.99 out of 5 average rating, 435 reviews

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

Guest favourite
A private heated pool is encased in a screened enclosure, featuring clear blue water. Adjacent to the pool, a hot tub is visible, offering a relaxing retreat. Access to the pool area is framed by glass doors leading from the main house.
Home in St. Augustine
4.88 out of 5 average rating, 112 reviews

Zen Oasis | Heated Pool | Hot Tub | Beach 12-Min!

Escape to our Zen Spa Retreat! Enjoy the soothing heated pool and hot tub, unwind on the expansive patio, or find tranquility in the zen-inspired interiors. This spacious 3 bedroom 2 bathroom is located in a quiet neighborhood close to Old St. Augustine, beaches and restaurants. Blackout curtains and smart TVs in every bedroom! Our fully equipped kitchen, washer, dryer, dishwasher, workspace and garage ensure convenience during your stay. Unwind in our serene oasis for the perfect Zen getaway.

Guest favourite
A swimming pool is surrounded by lounge chairs, with palm trees providing shade in the background. Blue skies and scattered clouds create a bright atmosphere. The pool area features a smooth surface and a safety railing on one side.
Apartment in St. Augustine Beach
4.84 out of 5 average rating, 267 reviews

Ocean Side Complex w/ Heated Pool B-15

Great Condo in a Beach Side Community But just to be clear Beach Side does not mean Ocean Front you will not be able to see the Ocean from the Patio The Condo is located next to Shopping Restaurants, and Historic Downtown, Great Beaches for a relaxing stay and 2 pools 1 heated Year Round Must be 21 years old to rent IMPORTANT! This unit is DOG friendly. No other pets of any type are allowed. There is a $100 Pet Fee due when you book a reservation. I have to register them before you arrive

Top guest favourite
The exterior of the casita features a gabled roof with large glass windows, allowing natural light to enter. Two double doors provide access, surrounded by lush green plants and palms. A covered entryway leads to the main entrance, enhancing the inviting appearance.
Guest house in St. Augustine
4.94 out of 5 average rating, 427 reviews

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

Top guest favourite
A tranquil outdoor space features a well-maintained heated pool surrounded by lush greenery and colorful flowers. Seating areas with black Adirondack chairs are positioned around the pool, offering a peaceful setting. A covered patio stands in the background, complementing the inviting atmosphere.
Guest house in St. Augustine
4.95 out of 5 average rating, 192 reviews

Heated Pool Beach Bungalow Steps to the Ocean

Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

Top guest favourite
A spacious bedroom is furnished with a king bed, complemented by decorative pillows and a throw blanket. A large area rug with colorful patterns covers the tiled floor. Natural light enters through two windows, framed by light curtains, while a bedside lamp adds soft illumination.
Guest suite in St. Augustine
4.95 out of 5 average rating, 751 reviews

Sheepdog Hideway - on Anastasia Island near Amp!

Awesome, private guest suite located on Anastasia Island near the St Augustine Amphitheater! Walking distance to Anastasia State Park! Enjoy staying on the island without all the hustle of a hotel. We have beach cruiser bikes available for use! We are 1.5 miles from the closest public beach access and a 3 mile bike ride to downtown St Augustine! Update for COVID-19 pandemic: We will be spraying all hard surfaces with EPA-approved sanitizer to do our best to make sure surfaces are safe.

Guest favourite
A private saltwater pool is surrounded by a spacious deck and lush greenery. Palm trees frame the area, offering a shielded retreat. A patio space is visible, providing comfortable seating options and direct access to the home.
Home in St. Augustine
4.95 out of 5 average rating, 146 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

Welcome to your peaceful Oasis. This home is beautiful, secluded, and fenced in 3/4-acre with nature at your back door. It's going to WOW you! There is plenty of room for everyone to spread out with an open floor plan. Includes: Pool Table, Dart Board, Board games, Hammock, Saltwater heated pool, & peaceful pond with waterfall. Come relax and have fun. Just minutes to Historic Downtown, Beaches, Restaurants & I-95. 30 min from Jax 40 mins from Daytona $100 pet fee & $50 a pet up to 3.

Superhost
A living area features a cooling ceiling fan and large windows with light-filtering curtains. A wall-mounted TV displays an aquatic scene. A light-colored coffee table sits on wooden flooring, complemented by decorative plants and a woven tray.
Apartment in St. Augustine
4.77 out of 5 average rating, 261 reviews

Great 1 bedroom 1 bath condo with heated pool

Great condo in an Oceanside community You cannot see the ocean from this condo 5-10 minute walk to the beach Private boardwalk to the beach Condo is in 3rd floor must climb stairs no elevator **** Tennis courts 2 pools 1 heated Shuffle Board Gym Restaurants and bars you can walk to Pet Friendly with a $100 pet fee Only 1 dog is allowed and we must register the dog before you check in The security will not let you on the premises if the dog has not been registered Pull out couch

Top guest favourite
A screened-in balcony offers views of the lush greenery and marshlands beyond. Colorful cushions adorn a comfortable seating area, while a small wooden table sits centrally. Natural light fills the space, creating a peaceful atmosphere for relaxation.
Apartment in St. Augustine
4.99 out of 5 average rating, 122 reviews

Riverfront direct views-Get it ALL in St Augustine

Do not compromise-Just get it all! This is the hidden gem you were waiting to find. Only a few minutes from historic downtown and the area's best beaches, The Conquistador offers 3 swimming pools, tennis, tennis/pickleball courts, trails, a fishing pier, playgrounds, BBQ area, pavilion and plenty of space to roam and relax under the amazing Oak canopy. The beach or Downtown a mere 12 minute drive. Stay in your very private condo and enjoy the gorgeous views of the Manatee River.

Top guest favourite
A light and airy living area features a comfortable gray sofa, a wooden coffee table, and a blue accent chair. A large flat-screen television is mounted on the wall opposite, while sliding glass doors provide access to a balcony area with outdoor seating.
Apartment in St. Augustine
4.97 out of 5 average rating, 187 reviews

Beach Condo, Pools, Bikes, Short Walk to Beach

Relax and unwind at our beautiful beach getaway. This one bedroom condo is located close to all St. Augustine has to offer. You can walk to the beach or take a quick drive to historic downtown. Ocean Village Club is a gated complex that has private beach access just a seven minute walk from your door, two swimming pools, tennis courts, grilling area, and free parking. This second floor unit is light and airy, immaculate, and beautifully decorated. We are family owned and operated.

Top guest favourite
The rustic boathouse is positioned near a scenic wooden dock extending into the river. Sunlight reflects off the water while a peaceful horse stands nearby, surrounded by lush greenery. The weathered exterior of the boathouse complements the natural setting.
Guest house in East Palatka
4.94 out of 5 average rating, 118 reviews

Charming Rustic Boathouse

Come stay at our rustic boathouse along the serene river. Its weathered, wooden, exterior exudes charm, adorned with unique decor. The sunlight reflects the water, casting shimmering light against the boathouse. Surrounding it, is lush greenery and trees that create a picturesque backdrop. Inside the boathouse is a cozy and inviting, with simple furnishings and the gentle scent of wood. It's a haven where one can escape the bustle of everyday life and embrace the countryside.

Guest favourite
The exterior of a one-story unit is displayed with a red metal roof and a welcoming porch. A colorful umbrella provides shade over outdoor seating. A grill is positioned nearby, and landscaped areas with flowers enhance the entrance.
Cottage in St. Augustine
4.91 out of 5 average rating, 279 reviews

Livin’ the Dream at St. Augustine Beach

Bright beachy unit with all amenities including community pool, close public beach access and essentials including bedding, towels, beach cruiser bikes and grill. Enclosed porch and outside deck are ideal for grilling out or hanging out. My home is located in Peppertree RV Resort . The public beach access is a short 10 minute walk away. The unit has parking for two vehicles with extra parking available in an overflow lot. A washer and dryer are located inside the unit.

Popular amenities for St. Augustine Shores rentals with a pool

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Quick stats about holiday rentals with a pool in St. Augustine Shores

  • Total holiday rentals

    Explore 20 holiday rentals in St. Augustine Shores

  • Nightly prices starting at

    St. Augustine Shores holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 790 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of St. Augustine Shores holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across St. Augustine Shores rentals

  • 4.9 Average rating

    St. Augustine Shores stays are highly rated by guests – averaging 4.9 out of 5!