Vacation rentals with a pool in Southside, Jacksonville

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Top-rated rentals with a pool in Southside, Jacksonville

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favourite

Home in St. Augustine

4.94 out of 5 average rating, 114 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.

Guest favourite

Home in St. Augustine

4.95 out of 5 average rating, 101 reviews

New LUX 4bed Saltwater, HEATED POOL, 2 Masters

Relax and have fun at this BRAND NEW LUXURY beach getaway with high end furnishings and linens. The house has 4 bedrooms including 2 masters w/ king beds, 3.5 bath and a chef’s kitchen! Minutes walk to beautiful and coveted beach (3 blocks) and a 10 minute drive to downtown St. Augustine where you can enjoy many restaurants, coffee shops and local boutiques. Best yet, come back home and relax in your own fully fenced backyard w/PRIVATE HEATED SALTWATER POOL. We promise you won’t want to leave!

Guest favourite

Bungalow in Springfield

4.98 out of 5 average rating, 390 reviews

❤️Private Pool Couples Getaway- Downtown

Our place is perfect for you and your loved one to escape your daily routine, recharge, relax and reconnect - Valentine's Day is coming! The getaway features: PRIVATE salt water POOL and Garden Spa-like bathroom with soaking tub, refreshing 24 inch rain shower. Smart TV+WIFI in every room including bathroom. Central location with close proximity to TIAA Bank Field, airport, Downtown, Florida Theater, Times Union PAC. Walking distance to local restaurants and breweries. Hope to see you soon!

Guest favourite

Home in St. Augustine

4.96 out of 5 average rating, 108 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!

Superhost

Home in Jacksonville

4.85 out of 5 average rating, 212 reviews

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.

Guest favourite

Apartment in Beaches

4.95 out of 5 average rating, 115 reviews

SleepyTurtle-BEACH FRONT BLISS!

Enjoy a stylish experience at this centrally-located place. Keep it simple at this beach front unit. Yes, it is 100% ocean front with only some grass and sand separating you from the water! With the pool and the beach just steps outside your door, "beachfront bliss" is exactly what you will experience! This gated property is within a short walking distance to all the great restaurants and nightlife the beach as to offer! Don't miss out on one of the best beach areas in Florida!

Guest favourite

Villa in Jacksonville

4.88 out of 5 average rating, 104 reviews

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.

Top guest favourite

Home in St. Augustine

5 out of 5 average rating, 127 reviews

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

Guest favourite

Apartment in Fernandina Beach

4.93 out of 5 average rating, 105 reviews

Hotel Side - Pool - Walk to beach and golf course!

This unit is located on the Omni Amelia Island Resort in a very safe area. This is the "Hotel" side of the 2-sided condo. This is a great space for a 2 couples or family to share a hotel style condo nestled right in the center of the Island. This unit is the just a short walk to the beach and new 10 hole par 3 golf course! - Pool - downstairs - Beach Access - 0.3 miles - New 10 hole par 3 course - 5 minute walk! - Quaint downtown Fernandina Beach - 15 min by car

Guest favourite

Home in St. Augustine

4.92 out of 5 average rating, 137 reviews

steps to the beach, double mastersuite- pool home

Cleaned using CDC guidelines- Oasis at the beach! Brand new home just completed and designed to be a vacation rental not modified to be one. Spacious 4 bedroom hosting 2 master suites downstairs accompanied with 9' ceilings throughout the first floor including the large living room that flows to the dining, guest bath, bar, chefs kitchen and eventually the doors out the back porch, pergola, grill area, paver patio and 10x20 pool with fully fenced in yard.

Superhost

Home in Jacksonville

4.85 out of 5 average rating, 134 reviews

Lux Oasis: *Heated Pool, Spa/Hot Tub&Grill Retreat

Discover your private oasis in the heart of Jacksonville’s charming San Marco neighborhood. This stylish 1950s home blends vintage charm with modern comforts—featuring a heated pool, hot tub, grill, and space for up to 8 guests. Whether you’re planning a family vacation, a weekend escape, or a long-term stay, everything you need for a relaxing getaway is right here. Pool heating available for $100/night with 48h notice. Hot tub heating is complimentary.

Top guest favourite

Home in St. Augustine

4.98 out of 5 average rating, 159 reviews

Tropical oasis in a family friendly neighborhood

In beautiful Vilano Beach Fl. New home built April 2019. Family neighborhood on dead end street. Beach entrance 50 ft to dune walkover. A 4 bedroom home has 2 masters downstairs, and 2 bedrooms upstairs with a play loft in between. Nearby restaurants, fishing, boating. Fenced back yard. We can heat the pool for $50 per day. bbq, and lounge chairs surrounding pool. Outdoor showers located near pool, beach toys , chairs.