Vacation rentals with a pool in Anastasia Island

An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.

4.99 out of 5 average rating, 158 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Experience the ultimate beachside getaway at our fully renovated Airbnb, just steps away from the sun-kissed sands. This luxurious retreat offers modern comfort with a private pool and inviting hot tub, allowing you to unwind in style. The recently upgraded interior boasts premium amenities, ensuring a relaxing stay. Outside, lush turf landscaping surrounds the pool, creating an oasis of comfort. Whether you're lounging by the pool, or enjoying the beach a stone's throw away, Driftmark delivers.

FamilyValueSleep quality

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, 448 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!

LocationFamilySolo travel

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, 231 reviews

Downtown • Historic Whitney House • Luxury Baths!

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.

ValueFamilyHeating

A view framed by lush tropical plants reveals the expansive waterway, with its calm, reflective surface. The image captures a serene outdoor space, featuring stone flooring leading towards the grassy area and water, emphasizing the natural surroundings.

4.97 out of 5 average rating, 114 reviews

Incredible Waterfront Townhome

As close to the water as you can get! Our building is considered the best in the complex which is waterfront, very private and peaceful. Perched on the Point we have fantastic views overlooking the intracoastal's oyster beds, mangroves, exotic birds, fish and bald eagles!. The sunsets are incredible. A fisherman's paradise. There is a private boat dock and a small boat ramp to launch your kayak. Watch dolphins put on a show almost daily from your lanai. The beach is right across the street!

FamilyValueLong stay

4.98 out of 5 average rating, 344 reviews

A private hot tub is set in a serene outdoor area surrounded by greenery and wood paneling. The tub is equipped with a cover and nearby is a container holding spa towels, providing a relaxing space for guests.

Villa in St. Augustine

Loins Bridge 0.5m away, 2 Bedroom, Private Hot Tub

Couples Retreat Near Downtown St. Augustine. 0.5 miles from the Bridge of Lions. Enjoy a secluded courtyard, relaxing water fountain, and new 4-person hot tub. Wine down and watch the sunset in a peaceful setting after a exploring. Off-street parking is included. Restaurants, bars, coffee shops, and local favorites are only steps away. Perfect for a romantic getaway, weekend escape, or special occasion. Special requests and accommodations are available to help make your stay unforgettable.

ValueFamilyQuiet

A modern white house is depicted with a covered entrance and a spacious patio area. A heated saltwater pool sits in the foreground, surrounded by a fenced yard. Two lounge chairs are positioned nearby, with a charcoal grill visible at the edge of the pool area.

4.97 out of 5 average rating, 115 reviews

Walk to Beach! Heated Pool•Boat Parking•EV Charger

This 2022-built luxury home is steps from the beach! It’s the ultimate basecamp for families, beach-goers, and boaters who want a stress-free getaway. 💧Heated Saltwater Pool: With an outdoor dining area 🏖️Location: A 4-minute walk to the fine-grain sand of Crescent Beach 🛏️ 2 Master Suites: This 4BR layout features two primary suites with private baths ⛵️ Boat Parking: Bring your boat or jetski . The Green Road Boat Ramp is 0.5 miles south 🔌Tesla EV Charging: Included in your stay

ValueLocationView

Guesthouse in St. Augustine

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.

4.95 out of 5 average rating, 213 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.

LocationFamilyParking

A serene sunset is captured over calm waters, reflecting warm hues of orange, pink, and purple. The horizon is lined with subtle clouds, enhancing the tranquil scene. The peaceful atmosphere invites relaxation and appreciation of nature's beauty.

5 out of 5 average rating, 129 reviews

Windjammer 208, Oceanfront and Riverview

Beautiful newly renovated condo in Crescent Beach, with spectacular views of the beach as well as the Matanzas river. Coffee while watching sunrise on your east balcony and wine while watching the sunset on the Windjammer fishing pier, while dolphins are entertaining you. 10 miles from historic St Augustine, a couple of miles from Marine land and a variety of restaurants close by. Flatscreen TV'S in all the rooms for your convenience when the weather does not allow you on the beach.

LocationFamilyGetting around

A private saltwater pool is centrally located within a spacious patio area, surrounded by well-maintained grassy lawns. Lounge chairs are positioned alongside the pool, while tables and chairs can be seen in the background. The home features sliding glass doors providing access to the pool area.

4.97 out of 5 average rating, 107 reviews

Music on Marilyn- Steps from the Amp! •Jacuzzi•

Nights of Lights & mere seconds from the St. Augustine Amphitheater— a short bike ride to the beach and downtown, this modern escape is 3 beds and 2 baths. Welcome to Music on Marilyn! This is the quintessential St. Augustine experience. Nestled on a quiet street that dead ends to the intracoastal, walking distance to the St. Augustine Amphitheater, Lighthouse, Anastasia Park, Alligator Farm and much more! St. Augustine Beach and historic downtown are just a short bike ride away.

FamilyValueTV

A large heated saltwater pool presents a curved design with a spa area seamlessly integrated. The pool area is surrounded by pavers and features vibrant turquoise lounge chairs. Lush greenery and decorative planters enhance the tranquil outdoor setting, enclosed by a white privacy fence.

4.99 out of 5 average rating, 124 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

Property Highlights - Large heated Saltwater Pool (heated Nov 1-May 1) - Hot Tub - Fully Fenced Private Backyard - Open Floor Concept - 1 Mile to Downtown - 1.5 Mile to State Park Beach - Quiet Neighborhood - Newly furnished Perfect for month stays, long weekend and week vacations, and out of town wedding guests! Escape to this St. Augustine home- that is not only the perfect vacation spot, but an ideal and convenient home away from home for your out of town wedding guests.

ValueFamilyPets

A comfortable living area is showcased with a light-colored sofa and armchair. Natural light flows in through sliding glass doors. A flat-screen TV is mounted on the wall, and a coffee table rests on a wooden floor, surrounded by decorative items.

4.95 out of 5 average rating, 188 reviews

Beautiful ocean, St Augustine beach

Close to shopping and restaurants. 15 min drive to historic downtown. Perfect for families, couples, friends, or solo travelers. Enjoy having no stairs to climb! Family friendly vacation. New king bed. Fully equipped kitchen, free WiFi, 2 pools (one heated), full size washer/dryer in unit, Smart TV, pet friendly 1 Dog Only, requires $50 (cash) registration fee upon check in. There is also a flat $15 Pet Fee for guests bringing a dog. **Strictly NON-SMOKING unit**

LocationFamilyCheckout

A bright living room features an open layout illuminated by natural light. Neutral-toned furniture is paired with colorful accent pillows. A natural jute rug lies beneath a low coffee table, while a ceiling fan enhances airflow. Large glass doors open to an outdoor area.