Vacation rentals with a pool in Historic District, St. Augustine

The front entrance features a pastel green exterior with a light purple door partially open. Two large lanterns flank the door, while lush greenery frames the pathway. A small mailbox is attached to the wall beside the door.

4.98 out of 5 average rating, 107 reviews

Walk to Everything plus Pool and bonus Cottage!

Our charming 4/3.5 home with heated saline pool is a quiet retreat from a day spent exploring beautiful St. Augustine! We are Downtown just blocks from the famed Fort. So close to the action you can park the car and forget about it! And best of all you really get 2 houses in 1 (double Kitchens and Livingrooms)! Perfect for extended families or friends catching up. If you need another rental we have a 4 bedroom with pool right next door. It's called Southern Charmer w/Pool - Walk to Everything.

A spacious backyard is highlighted by a private round pool, surrounded by lush greenery and palm trees. An outdoor cabana features a bar area, while a well-maintained lawn adds to the inviting atmosphere. The charming pink structure complements the serene setting.

5 out of 5 average rating, 124 reviews

Pink Palms *Heated Pool* Walk to Downtown

🏝️ Luxurious Private Heated Pool Home In Historic Downtown and Family Friendly! - Private Heated Pool & large backyard with tons of gorgeous palms - Outdoor cabana with grill, fans, pool table, kid toys, bocce, corn hole, recessed lights and seating - Walking distance to the Castillo de San Marcos Fort, Fountain of Youth, Uptown shops, The Bayfront and St. George Street - Less than 10 mins to Vilano Beach 🌊 - Sleeps 6/ 2 King beds, 2 XL twin beds (daybed trundle) - Pet Friendly - Event Venue

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.

4.99 out of 5 average rating, 437 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!

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.

4.94 out of 5 average rating, 216 reviews

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.

Guesthouse in St. Augustine

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.

4.94 out of 5 average rating, 437 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.

4.98 out of 5 average rating, 111 reviews

Htd Pool/Arcade, FirePit& PuttingGreen 1.2 mi 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

The exterior of the home features a two-story structure with a welcoming porch. Potted plants hang from the posts, and a decorative sign is positioned near the entrance. Lush greenery and various plants are arranged along the pathway leading to the front steps.

4.99 out of 5 average rating, 221 reviews

Historic St. Augustine 2/2 Duplex & Pool

About this space: Welcome to this 2 unit home located in Historic St. Augustine. This home is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This home has 2 bedrooms and 2 full bathrooms, a living room, kitchen, den and direct pool access. This space: This home is a 2 unit house Guest access: There is a lockbox on the door with a key inside Other things to note: Please keep in mind that the pool is a shared space :)

A serene backyard features a large swimming pool surrounded by mature greenery. Comfortable seating options are available, including lounge chairs and a small table with chairs, enhancing the outdoor relaxation area. Sunlight reflects off the pool's clear blue water, inviting refreshing moments.

4.95 out of 5 average rating, 112 reviews

Very Special Apt, St Augustine Historic District

Forget your worries in this spacious and serene apartment. A large, quiet space with a fenced beautiful backyard, large pool (rare for the Historic District) and gardens. Dogs are welcome. Just steps to what the walkable city of St. Augustine has to offer. A 3 minute walk to St. George Street for food, fun and frolic. The Fort, Castillo de San Marcos; the riverfront; Flagler College Tour; St. Augustine Lighthouse, restaurants & attractions close by. The beach is a 12 minute drive.

Condo in St. Augustine Shores

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.

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.

4.92 out of 5 average rating, 176 reviews

Covered seating is arranged around a sleek coffee table on a patio with a view of a large heated pool, accented by palm trees and umbrellas. A dining area with a table and chairs is visible, offering ample space for relaxation and enjoyment.

Condo in Lincolnville

F1, Downtown, POOL, beaches, porch, parking!

Relax in downtown St. Augustine, 5 - 10 minutes walk from Flagler College, and the main attractions. Large heated pool (April 1 -November 1) and back yard that is shared between our 4 apartments. This downstairs historic apartment has all the conveniences incl. TV's in living and bedroom, free WIFI and we offer Roku TV. We have a drip coffee maker, coffee, decaf, creamers, and sugar. Free parking for 1 car on premise and free street parking.

4.89 out of 5 average rating, 120 reviews

A backyard features a spacious heated pool surrounded by lounge chairs and tropical foliage. A large dining table with elegant chairs is visible, along with a covered gazebo. The exterior of the house showcases classic architectural details, contributing to the inviting outdoor atmosphere.

Home in Lincolnville

The Gatsby Mansion/Heated Pool/Heart of Town

Relax and experience 100 year-old “Classic meets Chic modern” architecture and design! Come enjoy lifetime memories with your family and friends in the heart of downtown Saint Augustine. Short walking distance to the heart of it all. >Pool! >Pool Heat available for $30 per day - Please inquire for terms and conditions >Mini golf course, corn hole, and **Wedding/Bach Groups please see additional information in other things to note section**

An outdoor seating area features modern gray chairs arranged around a fire pit, which is surrounded by soft sand. Lush palm trees and colorful plants provide a tropical backdrop, while the building's balconies overlook the inviting courtyard, illuminated by warm lights against a vibrant sunset sky.

4.97 out of 5 average rating, 113 reviews

> • Resort Style Retreat • <

🌴 Welcome to our cozy and stylish 1-bedroom, 1-bath apartment in beautiful Saint Augustine, Florida. Perfect for couples or solo travelers 💕, this peaceful retreat is nestled near the Intracoastal Waterway 🌊 and features a private balcony with scenic views 🌅. Just minutes from the beach 🏖️, historic downtown 🏰, and local dining 🍽️, it’s the perfect blend of relaxation and coastal charm ✨

Popular amenities for Historic District, St. Augustine rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An outdoor area features a small pool surrounded by lush greenery and a stone waterfall. Comfortable seating options include two lounge chairs and a sofa adorned with white cushions. A wall-mounted television is positioned above a rock feature, enhancing the space's leisure appeal.

4.95 out of 5 average rating, 22 reviews

Saragossa Poolside Paradise

A sparkling pool is surrounded by a well-maintained patio and vibrant landscaping. Lounge chairs are positioned around the pool, with a shaded umbrella providing additional comfort. Lush greenery and colorful flowers enhance the outdoor space, creating a welcoming atmosphere for relaxation.

4.96 out of 5 average rating, 51 reviews

Island Oasis - Between Downtown & the Beach

5 out of 5 average rating, 19 reviews

Cityside Sanctuary: Pool, Game Room, Steps to Town

4.95 out of 5 average rating, 110 reviews

An open concept living space is featured, showcasing a mix of comfortable seating options including a leather sofa and a spacious sectional sofa. Natural light floods the area, enhancing the wooden flooring. Decor includes stylish wall art and plants, adding a relaxed, beach-inspired vibe.

Home in Vilano Beach

Heated pool home with interactive gaming system

4.99 out of 5 average rating, 146 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

5 out of 5 average rating, 18 reviews

The Blue Dream Bungalow

4.92 out of 5 average rating, 108 reviews

Kid & Dog Haven: Poolside Fun in St. Augustine

A private heated pool is surrounded by a spacious patio designed for relaxation. Comfortable lounge chairs are positioned nearby, alongside a well-maintained yard with decorative plants. The pool house features a playful mermaid mural on its exterior, adding a touch of charm to the outdoor space.

4.93 out of 5 average rating, 138 reviews

Splash & Explore

Condo rentals with a pool

A scenic view reveals a sandy beach framed by rolling dunes and lush greenery. A wooden boardwalk leads to a shaded gazebo overlooking the ocean. The sky is clear with scattered clouds, creating a peaceful atmosphere by the water.

4.83 out of 5 average rating, 337 reviews

Shell Shack Resort - Beachside Condo

A large swimming pool is surrounded by lounge chairs under a clear blue sky, with palm trees swaying gently nearby. The pool's serene water reflects the adjacent condominium buildings, creating a tranquil atmosphere for guests.

4.91 out of 5 average rating, 244 reviews

The Salty Suite Resort style condo

4.95 out of 5 average rating, 197 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

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!

Condo in St. Augustine Beach

A person is seen in a casual pose near a life-size alligator statue on a wooden deck. The surrounding area features lush greenery, enhancing the natural setting. The alligator's mouth is open, and the wooden railing adds a rustic touch to the scene.

4.93 out of 5 average rating, 392 reviews

~Heated Pool~Hot Tub~Steps to the Beach~King Bed

A private balcony is presented, offering panoramic ocean views. The space includes a textured table and four chairs, with one set featuring floral upholstery. Green grass and sandy shorelines blend into the sea under a clear blue sky, enhancing the sense of tranquility.

4.98 out of 5 average rating, 102 reviews

Wade n Sea Ocean Front Condo

A bright living area features large floor-to-ceiling windows that provide sweeping ocean views. Comfortable seating is arranged around a central coffee table adorned with decorative items. A Smart TV is positioned for easy viewing, while a ceiling fan adds a cooling breeze.

4.97 out of 5 average rating, 134 reviews

Family Beach Condo - Steps To The Sand Or Pool

A cozy living area features a blue sofa accompanied by a decorative chair and a wooden coffee table. A ceiling fan provides airflow in the space. The open layout offers a view of the kitchen, where modern appliances and a breakfast bar create a welcoming atmosphere.

4.85 out of 5 average rating, 173 reviews

Ocean Side Complex with Heated pool B-24

Other vacation rentals with a pool

An outdoor area is depicted, featuring a salt-water pool surrounded by lounge chairs and shaded by a red umbrella. Permanent string lights provide soft illumination. Tropical landscaping and a covered space in the background suggest an inviting environment for relaxation and leisure.

4.94 out of 5 average rating, 33 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

Home in Ponte Vedra Beach

4.81 out of 5 average rating, 53 reviews

Oceanfront | Pool, Pet Friendly, Large Deck!

4.86 out of 5 average rating, 7 reviews

Marina Cove Coastal Haven|Pool, Games, Near Beach

4.95 out of 5 average rating, 39 reviews

Home in Lincolnville

Historic Recording Studio

Superhost

A welcoming living room is highlighted by two comfortable gray sofas adorned with yellow cushions. Natural light floods the space through large windows framed by sheer curtains, while a white coffee table lies in the center, complemented by decorative elements. The ceiling features exposed beams, enhancing the room's charm.

4.88 out of 5 average rating, 93 reviews

Beehive Bungalow -Historic Downtown-Heated Pool

A resort-style pool is surrounded by lounge chairs, palm trees, and blue umbrellas. The water sparkles under a clear sky. Modern buildings are positioned on either side, enhancing the spacious and inviting pool area.

4.93 out of 5 average rating, 82 reviews

St. Augustine Escape w/Pool, Gym, Games MORE!

The pool area features a large rectangular swimming pool with lounge chairs lining the sides. Palms and landscaped greenery surround the pool, creating a relaxing atmosphere. A warm sunset casts a golden glow over the scene, enhancing the coastal oasis vibe.

4.91 out of 5 average rating, 47 reviews

Luxury Costal Oasis Close to Beach & Amphitheater