Holiday rentals with a pool in Lakeside

4.99 out of 5 average rating, 150 reviews

Home in Avondale

Avondale Retreat - Private Home with Heated Pool

Enjoy the best of both worlds in Riverside! Walk or bike to many shops and restaurants in Historic Murray Hill, Avondale and Five Points, then return to your private, peaceful backyard oasis. Relax in your heated salt water pool, grill outdoors or prepare a meal in the fully stocked kitchen and wind down with a nightcap by the fire pit. Right off I-10 and I-95, close to the Jaguar Stadium, JAX, Mayo Clinic and only 25 minutes to Jax Beaches. Inquire about discounts for 3+week stays Nov-Feb

4.91 out of 5 average rating, 164 reviews

Home in Orange Park

Super Clean (Fantastic Pool) Home Near Everything

Your Home Away From Home Featuring A Fabulous Pool! You will say "Wow" as you walk in to your very private, very exclusive spacious 4 bedroom, 2 bathroom. Set in a quiet neighborhood thats still near everything. Grocery store, Orange Park Mall, 30 minutes from Downtown Jax, 30 miles from the beach. Sit back and enjoy one of 4 Tvs as you relax in the soothing ambiance. Want to cook? Perfect we have everything you need, and we have it twice! Fully equipped kitchen. Very Clean! BetterThan A Hotel.

4.99 out of 5 average rating, 150 reviews

Alice's Palace Alice in Wonderland St Augustine FL

Welcome to Alice's Palace; a sophisticated twist on Alice in Wonderland. This unique Madhatter tea party styled 1 bedroom condominium is like no other. It has a large fully equipped kitchen, spectacular forest King bedroom, onsite spa, stunning pool and hot tub. Located in the King & Bear golf community of World Golf Village and boasts 2 World Class Golf Courses-King & Bear/Slammer & Squire, pickleball and a gym. Just minutes from Outlet Shopping, Downtown St. Augustine and many amazing beach

4.98 out of 5 average rating, 400 reviews

Bungalow in Springfield

❤️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!

Campervan/RV in Jacksonville

4.97 out of 5 average rating, 197 reviews

Couples clothing optional escape hot tub nude deck

You'll love this unique and romantic escape. Designed to create an intimate setting to enhance your time together. The RV is quite large and fully equipped . Master bedroom features a cashmere topped California king bed. The property has so many amenities starting with a very large pool, lighted at night. A dock on the river to enjoy the views. Access to kayaks on premises. There’s a private clothing optional area/deck with a massage table , hot tub and loungers. We recently added a fire pit

4.87 out of 5 average rating, 391 reviews

Condo in St. Augustine’s World Golf Village Resort

Escape to St. Augustine and enjoy a one bedroom studio with new brand new renovations and upgrades! Explore the resort amenities including free unlimited access to three pools, a hot tub, lighted tennis and pickleball courts, playground, and fitness center. Located within the private gates of the World Golf Village, home of the King and Bear Golf Course. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

4.86 out of 5 average rating, 182 reviews

Home in Orange Park

Cheerful three bedroom home with a pool

Relax with the whole family at this peaceful place to stay. Enjoy the pool or just lay out in the pool area with friends. Have a bbq and enjoy family. Spacious backyard with two hammocks and a tree swing. Front porch has a nice sitting area and tree swing. Connect to your favorite streaming platforms on the smart TV's, tv room has karaoke and free WiFi. Board games in hall closet to enjoy with family. 3 miles from Orange Park Mall, AMC movie theatre and many restaurants just minutes away

Home in Southwest Jacksonville

4.92 out of 5 average rating, 138 reviews

Cozy Home with Heated Private Pool and Patio

Nice and very clean house for your vacation and a comfortable stay. Cozy sitting area with a small pool. A protective screen around the recreation area will keep you from Florida insects))). Parking for 4 cars. Our home is located in a very convenient location: Less than 1 mile to the main road I-295 as well as the Costco store and Walmart Supercenter. At the same time, the house is located in a quiet area where you will not be disturbed by the various noises of city life.

4.93 out of 5 average rating, 310 reviews

Home in Riverside

Historic Hollywood House w/Pool

Located in Avondale, this well kept 98 year old house features original hardwood floors throughout, updated kitchen. There are 2 main bedrooms, and a third with a twin bed + trundle but no door. The back yard is private with a beautiful pool (that is not heated) and cabana. Be sure to read the house rules and neighborhood description so that there are no surprises after your reservation is confirmed. Ring cameras monitor all the entrances and are motion activated.

5 out of 5 average rating, 128 reviews

Home in 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

4.84 out of 5 average rating, 139 reviews

Home in Jacksonville

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.

4.89 out of 5 average rating, 201 reviews

Guesthouse in Avondale

Cute Pool Cottage in the Historic District

Poolside guesthouse in a lush tropical garden yard-this studio with 1 bedroom/1 bath is in Jacksonville’s Avondale Historic District, and just steps away from the popular Shoppes of Avondale with its restaurants and quaint shops. Its perfect for business travelers, singles, or couples. The space features a super cozy queen size bed with luxury linens. There is also a mini-kitchen with microwave, toaster oven and compact refrigerator. There is no stove.

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House rentals with a pool

4.91 out of 5 average rating, 164 reviews

Home in Jacksonville

Cozy ranch near Jax

LaurenRating, 5 stars1 month ago

April’s place was exactly as described. There are thoughtful amenities and plenty of space. The location was very convenient to the airport. After a small miscommunication, April went above and beyond to make sure we felt comfortable.

Home in Southeast Jacksonville

4.86 out of 5 average rating, 207 reviews

Private FL Home with Pool, Hot tub & Luxury Master

JoanRating, 5 stars2 weeks ago

Sandra was a terrific host. her place was as described even better. beds were comfortable,lots of bathrooms, lots of outdoor seating, and pool toys and indoor and outdoor toys/games. perfect for us as we had a family wedding in the area. neighborhood was nice, quiet nearby to stores and restaurants.

Home in Southeast Jacksonville

4.79 out of 5 average rating, 120 reviews

Private Pool Home • Quiet • Near Beaches & Dining

LoriRating, 5 stars2 weeks ago

Pool was lovely. Layout was very open. Such a nice place for us as well as our dogs.

Home in Southeast Jacksonville

4.8 out of 5 average rating, 110 reviews

~Green Felt Getaway_Sleeps 12_Heated Pool & Spa~

MaryRating, 5 stars1 month ago

This house is in a great location and super spacious for a large group. It has good gathering spaces, both inside and out. It was very clean inside. I would have never guessed they will allow pets. The kitchen is sparsely furnished so cooking in was a bit of a challenge. The bedroom with two twins is only separated from the kitchen with a curtain, so noise could be a factor. The pool and hot tub were well maintained, but the deck area needs some sprucing up.

4.82 out of 5 average rating, 11 reviews

Home in Middleburg

The Retreat ~ Pool ~ Gameroom

AllenRating, 5 stars1 day ago

It was a nice and comfortable stay felt like I was right at home. Lots to do in the area and couldn’t have asked for a better house. Really enjoyed our stay and made some great memories.

Home in Southwest Jacksonville

4.95 out of 5 average rating, 166 reviews

+A Taste of Britain entire house / heated pool+

NeftaliRating, 5 stars1 week ago

Can't say enough about how great a host James was. He was responsive in a timely manner everytime I had a question. The place was immaculate!! A well spent Birthday getaway!!

4.91 out of 5 average rating, 153 reviews

Home in Jacksonville

The Pink Cabana

Ma'KaylaRating, 5 stars2 days ago

The house was amazinggg! It was literally like a girly girl house & was super pretty and it was just so relaxing! Definitely loved the aesthetic & the pictures on the walls! Felt like I was out of town even tho I was still in jax! The pool was also veryyy pretty! If I had to stay again I most definitely would!!! 10/10!!

4.98 out of 5 average rating, 106 reviews

Home in St. Augustine

Driftmark Cabin - RV friendly, Pool + Beach!

CaraRating, 5 stars3 weeks ago

The house was perfect for us and the dogs! The beach is a hop and skip away loved the pool very spacious place! The downstairs was a plus having two washer and dryers also very spacious upstairs and downstairs! Everyone felt like they had there on little space and not on top of each other. The ice machine downstairs was so convenient for the coolers to go straight to the beach! We will defiantly be back it was the perfect place for us!

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Condo rentals with a pool

4.94 out of 5 average rating, 126 reviews

My HOUSE is your HOUSE

RodneyRating, 5 stars3 weeks ago

We had a great stay. The condo was lovely, clean and beautifully appointed. Our host was very helpful and communicative. We loved the area and the property overlooking the gorgeous pool. We highly recommend this property and would love to stay again.

4.88 out of 5 average rating, 155 reviews

Luxury 2/2 condo w/patio, beautiful golf community

LauraRating, 5 stars2 weeks ago

This was our 4th time staying here. Always a blessing! Convenient to everything and we enjoy the amenities.

4.93 out of 5 average rating, 111 reviews

Spanish Colonial Design One Bedroom Condominium

HannahRating, 5 stars2 weeks ago

Nicki’s place was a perfect, peaceful and private getaway for my husband and I. We thoroughly enjoyed our stay! Close to a Publix and quick bites. Only a 25 minute drive to historic St. Augustine, and 35 minutes to the beach. We felt safe in the gated community and enjoyed the pool/hot tub.

4.92 out of 5 average rating, 312 reviews

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

JenniferRating, 5 stars5 days ago

We very much enjoyed our stay! The condo was amazing. The pools were very clean and peaceful. Our host was very responsive and kind. The walk to the beach wasn’t that bad at all! I loved the security features and felt safe with my daughters. I would recommend this condo to friends, and would stay here again.

4.97 out of 5 average rating, 197 reviews

Condo in Beaches

Beachcomber Oceanfront 180* panoramic view

TabithaRating, 5 stars2 weeks ago

Very nice place...really clean and peaceful.

4.9 out of 5 average rating, 101 reviews

Condo in Beaches

Oceanfront Condo with Views, Pool, Park

SavannahRating, 5 stars1 month ago

My family two babies and a dog stayed here for a long weekend trip. It accommodated all of our needs and was easily located to pool beach. The park right next door was ideally the best part for babies and dog. Would stay here again

Condo in Fernandina Beach

4.99 out of 5 average rating, 135 reviews

Resort~ Amelia Island~ Ocean Front~ Condo

LillianRating, 5 stars2 weeks ago

This was a top tier stay! The unit was beautifully decorated, super clean, and very well stocked! Did I mention the incredible views? 😍 Brook was an amazing hostess and made sure we had all of our questions answered and everything we needed. Highly recommend!