Holiday rentals with a pool in St. Augustine

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.

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.

Lux Retreat|Private Pool|Walk to Historic DWTN

Relax & Reset at The Retreat - a rare private in-town getaway for two couples. Sparkling pool & tropical outdoor oasis in gorgeous designer home. Located on quiet street, 8-min walk to Historical Downtown and the hottest bars & restaurants. Spread out in 1800SF of dramatic light filled spaces - 2BD/2BA has been completely reinvented for casual, elegant living. Each bedroom features unique architectural treats - a private balcony to the east and a sun-drenched studio kitchenette to the west.

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

* Built in 2023- luxe coastal furnishings & linens * Featured in 2024 Good Housekeeping Mag🌟 * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool & Spa/Hot Tub * Poolside Cabana | Outdoor Kitchen | Front Porch * Bikes, Beach Toys, Beach Chairs * Lush Tropical Landscaping * 0.2 miles - gorgeous quiet beach * 5.5 miles- historic downtown St Augustine- The oldest city in the United States! * 0.2 miles - Cap's Restaurant for sunset dinner on the water

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

Have fun with the whole family at this playful Floridian cottage full of artful amusements and creature comforts. Catch 33 features a private heated pool and is only steps from the sands of Vilano Beach. Here, you will enjoy solitary mornings collecting shells, a roomy shore for sunbathing, local seafood restaurants, a pier for fishing and a glowing sunset. In under 10 minutes, you can immerse yourself in 450 years of colonial history, a lively music scene and vibrant culinary experiences.

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.

4Bed, 3Bath-Heated Pool & SPA-Don't You Wanna?

Don't You Wanna...4 Bedroom, 3 Bath with HEATED POOL, SPA, and Outdoor Shower located in the heart of Vilano Beach of historic St. Augustine, FL. Our conveniently located home allows you to bring family and friends to share memories with a nice sunset or sunrise just down the street at the third street beach access point. Want to have a nice dinner at one of the most popular restaurants in all of St. Augustine? Walk around the corner to Cap's On The Water for great dining.

Dune Bungalow

Cottage style home with comfortable porches to enjoy sound of ocean waves breaking on the front and back porches. Pool in the back yard (heated by request for $50 per day) cookshed, fenced with lush trees and woods to the east. The inside looks large with high wood ceilings and multiple windows and glass doors to the beautiful pool area. Located on a dead end street in a family neighborhood with 5 star restaurants nearby. Fifteen minute drive to downtown St. Augustine.

Private oasis, private pool, exceeds expectations

Three bedroom home located on 2 acres. Only 25 min from down town historic district of St Augustine Fla Private Pool Pool house for kids to hang out in and play games / with patio and fire pit Property gated with remote control entrance gate Has chicken for daily fresh eggs Can park camper on property Has screened porch Cable TV in living room, master and guest bedrooms Free wifi TVs in master, main living area guest room and pool house Covered parking Security system