Fitness-friendly holiday rentals in Anastasia Island

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, 344 reviews

Shell Shack - Resort Beachside Condo

Beautifully decorated & upgraded beachside 2 bed/2bath ground floor unit with an assigned parking spot right next to your patio entrance. Natural light fills the condo. The patio gets plenty of sunshine from its southern exposure positioning so it offers a great place to enjoy your coffee in the morning, wine at night, or to catch up on your tan. The sunshade allows for a private outdoor experience when you just want to sit quietly alone listening to the ocean waves crashing along the beach.

Apartment in St. Augustine Beach

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.

4.85 out of 5 average rating, 281 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

4.94 out of 5 average rating, 225 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 • 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.

The living room features a sliding glass door that provides a direct view of the beach. A comfortable sofa is positioned near a coffee table, while a side table and chair complement the seating arrangement. Natural light brightens the space, enhancing coastal decor.

4.99 out of 5 average rating, 136 reviews

361 Fun in the Sun | Direct Oceanfront Ground Floor

Direct Oceanfront, ground floor flat unit, no stairs. Located in Crescent Beach at Summerhouse. Family oriented complex located on over 25 acres with four pools and large grass areas. Highly desired 2 bedroom unit. This property is ground level and directly oceanfront. Flat style layout not a townhouse, there are two steps to the front door but otherwise no stairs. Sliding door opens directly to covered back porch. Please see our our other property 461 More Fun in the Sun, 3 Bedroom

Superhost

The living area is furnished with a comfortable sofa and armchair, providing a relaxed seating space. A media console holds a television, and large sliding doors lead to a private balcony. Natural light fills the room, highlighting a neutral color palette.

4.9 out of 5 average rating, 374 reviews

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

1 bedroom condo with King Size Bed, Sleeper Sofa, 55" TV's in Living Room and Bedroom. Stairs to 3rd Floor unit with private patio. Fully Equipped Kitchen, Dishwasher, Washer/Dryer, WiFi, Cable TV, Clubhouse, Fitness Room, Tennis Courts, 2 Swimming Pools (1 heated), Shuffleboard Courts, Picnic Area with Grills & Private Beach Walkway about 5-10 minute walk to the beach and pools . Dog Friendly (1 DOG ONLY) with a $100 pet fee due on Check In. Must be able to climb stairs 3rd floor condo

A spacious outdoor pool area is surrounded by lounge chairs and palm trees, providing a serene environment for relaxation. An adjacent building features balconies, offering views of the pool. A pergola is visible nearby, complementing the inviting atmosphere of the gated community.

4.93 out of 5 average rating, 129 reviews

Sun & Sea - Beach & Heated Pool, Pet Friendly!

Indulge in the comfort and style of this spacious one-bedroom king bedroom couple's retreat. Situated on the ground floor, this end unit is conveniently located within walking distance of restaurants and shops. This oceanfront complex offers top notch amenities, including a beach walkover, two pools (one heated), tennis courts, shuffleboard, a well-equipped gym, and a grill area, all within a secure gated community. Enjoy coastal proximity, with downtown St. Augustine only 10 minutes away.

A vibrant view shows lush green lawns and palm trees leading to the outdoor pool area, with the ocean visible in the background. Two white buildings frame the scene under a clear blue sky, emphasizing the serene coastal atmosphere.

4.86 out of 5 average rating, 125 reviews

Heated Pool, Ocean Views, Beach, Playground, BBQ

Save my home to your wishlist by clicking on the heart in the upper right corner! *Book 3 nights, get the 4th night 30% off!* >100 Steps from the beach! >Ocean and Pool Views! >Indoor heated pool, outdoor unheated pool, jacuzzi! >Sauna, tennis, racquetball, fitness center >Downtown St. Augustine is a 17 minute drive >Cable TV and streaming apps. Fast Wifi. >Drip coffee maker >Washer + Dryer in the condo >Spacious private patio >2-3 days of supplies provided (TP, trash bags, pods, etc)

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.

4.92 out of 5 average rating, 252 reviews

The Salty Suite Resort style condo

This modern 1 bed/1 bath rental unit has access to a private walk way to 2 pools, beach (5 min walk from door to sand) & tennis courts all in a gated community right on famous A1A in the Oldest City in the Nation. Perfectly situated by the beach or a quick Uber ride to Downtown to check out the history of the Oldest City in the Nation & try some other great local restaurants. We provide an in room guidebook telling you all the must do's in the town & helpful hints too! See you soon!

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.

4.93 out of 5 average rating, 110 reviews

Hideaway at Crescent Breach - St. Augustine

Recently updated, two-story townhouse, just steps to the beach! We have everything you need for a relaxing vacation on Crescent Beach in St. Augustine!, FL! Amazing views! Great for families and snowbirds alike! Weekly & monthly discounts available. Wide beaches, temp-controlled swimming pools, pickleball, tennis, racquetball, a basketball area, a new children's play area, and a lending library with books, puzzles, and games. This is the PERFECT place for families and active adults!

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.

4.97 out of 5 average rating, 205 reviews

St Augustine Beach Condo, Pools, Bikes, Beach Gear

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.

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.

4.94 out of 5 average rating, 175 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**

A spacious heated pool is surrounded by palm trees and lounge chairs, offering ample seating. A shaded pavilion adds to the inviting atmosphere, while clear blue skies and fluffy clouds create a serene backdrop for relaxation. The area features tiled edges and a clean, well-maintained appearance.