Vacation rentals with a pool in Lakeside

5 out of 5 average rating, 140 reviews

Southern Charmer w/Pool - Walk to Everything!

Stellar location...easily park and walk to historic sites! Spacious and modern inside but a classic Southern home on the outside. Lots of room to grill out or lounge around the heated saline pool. Beautiful views of the famed Mission from the upper/lower porches. And you'll appreciate how well stocked this home is too...if we don't provide it you probably don't need it! If you need another rental we have a 4 bedroom w/pool right next door. It's called Walk to Everything plus pool and Cottage.

4.96 out of 5 average rating, 187 reviews

Home in Lincolnville

Walk downtown, pool beach min to everything pet ok

HEATED pool home in the heart of historic St Augustine, Walk to the NIGHT OF LIGHTS; just a few miles from spectacular beaches! Weddings/Family time. 4 large bedrooms with 3 full baths. 1 bedroom downstairs and 3 upstairs. Relax in the screened in lanai with beautiful lap pool! Large back yard. Enjoy cooking in our huge kitchen while your family relaxes in the living room, or have enjoy playing foosball after a day at the beach or touring our beautiful city! Walk to everything! Pet friendly

Top guest favorite

4.94 out of 5 average rating, 113 reviews

CLUB MED•Paradise • Privacy • PETS Ok•BIG PooL•

This beautiful home (2000sqft) is just a few blocks from the ocean which has easy beach access,including a play ground for children. Then a street over is the river which has boat ramp! You can also enjoy a local neighborhood restaurant just down the street with a water front view where the sunsets are mesmerizing! The home has been completely remodeled and has a gated back yard with a big pool for you and your family to enjoy. It is also a short drive to the historical down town St.Augustine.

4.96 out of 5 average rating, 105 reviews

New luxury heated pool home steps from the beach!

Welcome to the Coral Door House! Tranquil retreat at the beach. Newly built spacious and modern luxury home. A private entrance to a very special and secluded beach is just 6 houses down. An easy short walk with the stocked provided beach cart. Outdoor living space has a 10 X 20 heated pool and plenty of seating. A perfect place to relax after a day at the beach. We’d love to host you and your family so let us know when you want to come stay, and we can discuss more details from there!

4.85 out of 5 average rating, 207 reviews

Home in Jacksonville

Sunny Florida home with a pool.

Enjoy a stylish experience at this beautiful home that is 16 minutes from the beach, 15 mins from Mayo Clinic and downtown. This home has two bedrooms, two bathrooms, living room, porch, and swimming pool. The living room has a couch that unfolds to a bed. The pool has a screen room around it to keep all the bugs out. There is a smart tv in each bedroom and living room. The house also includes high speed internet and a fence around the backyard. You can enjoy a nice cookout in the backyard.

4.97 out of 5 average rating, 130 reviews

Home in Lincolnville

Southern Comfort - Downtown|Hot Tub|Heated Pool

The Southern Comfort is a 4BR/3.5BA home located right in the heart of Downtown St. Augustine on the famous King Street. High-end, designer touches will be found in all features of the home with respect to the 110+ year old character preserved in the 2020 renovation. Centrally located with a blend of privacy, convenience and a modern luxury design. Private, sparkling heated pool and hot tub with lounges perfect for lazy days by the water. #1 Vacation Rental in Downtown St. Augustine.

4.87 out of 5 average rating, 124 reviews

Best of Both Worlds- Family Oasis

Experience the Dolphin house in St Augustine. This spacious mid-century modern pool home is a rare treasure in an ideal location just steps from the Bridge of Lions and downtown St Augustine. The Showstopper Private Backyard oasis includes a pool with a shelf - perfect for kids, Hot Tub, BBQ, Hammock, Wood Fire Pit, and outdoor seating under a mega umbrella. The perfect family vacation getaway. Maximum occupancy of six (6) adults and four (4) children under twelve (12) years of age.

4.78 out of 5 average rating, 231 reviews

Condo in St. Augustine

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

Condo in St. Augustine Beach

4.85 out of 5 average rating, 161 reviews

Ocean Side Complex with Heated pool B-24

Ocean Side Condo Complex. Just to be clear Ocean Side does not mean Ocean Front. You will not see the ocean from the balcony 1 Bedroom 1 Bath. There is a queen air mattress that 2 people can sleep on and can be put in the living room 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 No trailers or boats allowed or campers

Top guest favorite

4.96 out of 5 average rating, 276 reviews

"The Pink House" Uptown St Augustine Charmer

Visit Historic St. Augustine & truly "Have It All!!" Walk to downtown sights, trolley, fort from your expansive secluded oasis. Our lovingly decorated and well stocked home features a wraparound porch. Spacious outdoors, shared amongst just 4 rental properties, with resort-quality pool+cabana, multiple seating areas, argentine grill, hammocks. Book our co-listings upstairs - "The Attic" or guest cottage "The Little Pink House" to add another bed + bath for your group!

4.88 out of 5 average rating, 101 reviews

Villa in Jacksonville

Country villa pool hot tub game rm pond 2.5 acres

Take it easy at this unique and tranquil getaway. Ask about our couples discount. Our villa includes pond, pool, hot tub, game room, outdoor cooking area with industrial smoker, wood burning pizza oven, and gas grill. Oyster bar, fire pit area wood included. Kitchen has 2 coffee making options, air cooker and all other essentials. Full laundry with soap and dryer sheets. Parking space for your toys and camper. Security gate w/ fence completely surrounding the property.