House holiday rentals in Fleming Island

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Popular amenities for house rentals in Fleming Island

House rentals with a pool

Guest favourite
Home in St. Augustine
4.96 out of 5 average rating, 105 reviews

New luxury heated pool home steps from the beach!

GeorgiaRating, 5 stars1 month ago
Our stay was absolutely perfect! The house was beautiful, clean, and had everything we needed for a comfortable stay. The location couldn’t have been better—just steps away from the beach, making it so easy to enjoy the ocean any time of day. Eason was an amazing host, incredibly responsive and helpful throughout our stay. We couldn’t have asked for a better experience and would definitely stay here again! Highly recommend!
Guest favourite
Home in Orange Park
4.83 out of 5 average rating, 168 reviews

Stunning Modern Oasis with a Huge Pool

BriggettRating, 5 stars2 weeks ago
House was everything I imagined from the pictures. I really enjoyed every moment of my stay. Well worth it!
Top guest favourite
Home in Southwest Jacksonville
4.96 out of 5 average rating, 163 reviews

+A Taste of Britain entire house / heated pool+

TrishRating, 5 stars2 days ago
Kids loved the pool. Had an awesome stay. James was very responsive. Will definitely be our go to in Jacksonville.
Top guest favourite
Home in St. Augustine
5 out of 5 average rating, 125 reviews

Private oasis, private pool, exceeds expectations

StefanieRating, 5 stars2 weeks ago
We had such a special weekend at this beautiful property. The space was peaceful, fun, and full of charm — perfect for making memories with family. Every part of the house and grounds felt so thoughtfully put together, with little hidden gems to discover everywhere you looked. Collecting eggs each morning turned into a fun little game, with everyone trying to call dibs on who got to do it that day. The man cave was a major hit — packed with personality and details that made it feel like staying at a friend’s place. We also loved spending time by the pool and relaxing in the screened-in patio — the perfect spot to wind down in the evenings. Thank you for sharing this one-of-a-kind home with us. We’re leaving with full hearts and some unforgettable memories.
Top guest favourite
Home in St. Augustine
4.98 out of 5 average rating, 165 reviews

Historic St. Augustine 2/2 Duplex & Pool

PamelaRating, 5 stars2 weeks ago
Lili’s place is beautiful!! My mom and I had a wonderful time! Lili’s home made us feel like we were home. We had a chance to meet Lili and she is very sweet and kind. Thank you again for your hospitality!! We will be back!!
Top guest favourite
Home in St. Augustine
5 out of 5 average rating, 140 reviews

Southern Charmer w/Pool - Walk to Everything!

TiffanyRating, 5 stars2 weeks ago
Came for a wedding. The home was exactly as the pics showed and it was pristine inside with all the necessities including beach chairs, umbrellas and towels. Perfect location, walkable quaint little area, lots of great recommendations too. Great space, amazing host, Pauline always responded quickly and went above and beyond to accommodate us. We thoroughly enjoyed our time there, just needed another day or two to enjoy the town. Highly recommend.
Guest favourite
Home in Orange Park
4.87 out of 5 average rating, 175 reviews

Cheerful three bedroom home with a pool

AnnsleyRating, 5 stars1 week ago
Beautiful space! Absolutely recommend and will be staying here next time we are back in town!
Guest favourite
Home in Lincolnville
4.96 out of 5 average rating, 188 reviews

Walk downtown, pool beach min to everything pet ok

Linda ShorkeRating, 5 stars2 weeks ago
We had a wonderful family reunion at Theresa’s lovely house. There was something for every age group to do. The yard was very private and yet you could walk to coffee shops and even to downtown. The pool was wonderful and the house was spacious. The host was very accommodating and even my dog felt welcomed! Would definitely recommend and plan on staying again.

Weekly house rentals

Top guest favourite
Home in Beaches
4.99 out of 5 average rating, 154 reviews

Renovated Beach House w/ Pool and Outdoor Oasis

LisaRating, 5 stars6 months ago
Leslie and Joe were so welcoming and friendly and helpful. Their home was perfect for us. The house is a true beach house just a quick drive across the street from the ocean. The back yard is beautiful and the pool and jacuzzi were a nice way to help ease the stress of the storm. We actually came during Milton the Hurricane. We were seeking a safe place from the Tampa Bay Area. They were both able to ease massive anxiety by being so accommodating and we greatly appreciate everything. Can’t wait to visit again for a true vacation.
Guest favourite
Home in Orange Park
4.9 out of 5 average rating, 231 reviews

Luxury Home w/ Glass Room & Patios

AnnaRating, 5 stars2 days ago
Lori’s home was a perfect landing place for our family. We were in town for a funeral and this home allowed us more time to be together. It was well furnished and housed 10 people comfortably with some room to spare.
Top guest favourite
Home in Jacksonville
4.99 out of 5 average rating, 195 reviews

The Hothouse-Couples Escape: Play-Relax-Reconnect

NajiahRating, 5 stars2 weeks ago
I decided to book this place to celebrate my boyfriends 25th birthday. It looks like a page from magazine. This was a spectacular sensual mini staycation. It’s exactly what we both needed. Directions for utilization were precise & clear. I adored all of the sexy decor, sleek appliances and supplied amenities. The bed felt as if we were sleeping in the clouds. The space is absolutely spotless and smells wonderful. The time went by too quick ! We will definitely be back! Thank you Juliana & Mike.
Superhost
Home in Southeast Jacksonville
4.8 out of 5 average rating, 101 reviews

Cozy 3BR Home near San Marco - Sleeps 6

KatyRating, 5 stars3 weeks ago
Lisa's place will hold a special place with my family. we had a wonderful time and loved every minute spent at "home"
Guest favourite
Home in Beaches
4.95 out of 5 average rating, 20 reviews

Coastal Chic Chalet

MartinRating, 5 stars1 week ago
I would rate this higher than five stars. The location was perfect for us to join the GORUCK HQ Ruck club for workouts and social gatherings. It was very easy to reach the beach. The beach chairs were a bonus for us to use as well. Everything about the home was excellent. We enjoyed soaking up the rays in the backyard, followed by a meal in the back under the giant shade tree. The furniture was all very comfortable. The kitchen had everything you needed for cooking meals at home. We look forward to a return visit to Jax Beach and making this our rental again.
Superhost
Home in St. Augustine
5 out of 5 average rating, 7 reviews

MEMDAY Deal! Fam Trip_PrivatePool_3miles to Beach

GarrettRating, 5 stars1 month ago
Lipsy was a very helpful host! She was quick to assist with everything! The house is located less than 10min from Historic St Augustine so it’s perfect! We had a large group and it fit us perfectly. The 2 kitchens allowed us to store and prep all the food we needed. The backyard was great for kids and the open space allowed us to spread out! If we go back we would stay here 100%!
Superhost
Home in Jacksonville
4.9 out of 5 average rating, 29 reviews

30+day Rental, minutes from Beach, Mayo, Downtown

LidiaRating, 5 stars3 weeks ago
Comfortable home, clean and easy access to to hwy and parks nearby.
Superhost
Home in Beaches
4.88 out of 5 average rating, 112 reviews

Luxury Pool House Perfect for Family Getaway

JosephRating, 5 stars2 days ago
Was definitely one of our favorite places we have stayed in! The house was clean, spacious and provided lots of entertainment. We loved the backyard including the pool, corn hole boards and especially the ping pong table. The owners seem to have thought of everything. Communication was simple and easy. Can’t recommend enough. We went on family vacation with 6 adults, 1 baby and 2 small dogs. Plenty of room for all. Great water pressure for showers and plenty of hot water for all. Kitchen with bar area up to date and spacious. Thank you for making our place to stay safe and highly enjoyable!! Hopefully we can return one day.

Private house rentals

Guest favourite
Home in St. Augustine
4.93 out of 5 average rating, 164 reviews

5*Pool Oversized Home*Beach*Walk to all

TomRating, 5 stars5 months ago
We loved staying here. Beautiful home, extremely comfortable and very convenient to the old town. A nice surprise that Nancy decorated for Christmas with a tree, lights, etc. and set the mood for our Thanksgiving week with the town’s lights.
Superhost
Home in St. Augustine
5 out of 5 average rating, 3 reviews

Sand and Waves: side by side Beachfront Bliss

MarkRating, 5 stars2 months ago
We stayed at Paola's place for a company retreat. We were able to book both houses and they very comfortably accommodated our group of 14, with room to spare. The houses were very comfortable. The property is amazing, with direct beach access and plenty of room. Paola was a great host. Very responsive and very helpful. I would definitely stay again.
Superhost
Home in Springfield
4.79 out of 5 average rating, 24 reviews

Blue Haven

TomRating, 5 stars2 weeks ago
Host was able to meet my groups unique needs, included some last minute changes!
Guest favourite
Home in St. Augustine
4.98 out of 5 average rating, 116 reviews

Country Cottage 3-bedroom home with free parking

PamelaRating, 5 stars1 week ago
Absolutely spotless accommodations! We loved this home and plan to return!
Superhost
Home in St. Augustine
4.74 out of 5 average rating, 127 reviews

Uptown "Hide-Out" Stylish Home in Prime Location

LonRating, 5 starstoday
This is a very nice and clean home in s great location. We were within walking distance of the Castillo so we were able to leave the car parked and walk around all day. I will definitely stay here again.
Guest favourite
Home in Beaches
4.93 out of 5 average rating, 28 reviews

Private Beautiful Beach House - steps to the beach

TKeyahRating, 5 stars1 week ago
Overall it was a great stay. It was convenient because the beach was literally across the street. We we didn’t burn any gas riding around looking for things to do. Me and my kids loved it. The pictures on the profile could be better because I actually thought the living room and kitchen was bigger but that didn’t matter honestly. Publix and everything else was down the street! This stay is literally 30 mins away from the zoo , this is a great location for a getaway! Thanks!
Top guest favourite
Home in Southwest Jacksonville
4.97 out of 5 average rating, 256 reviews

Single House: 12guests/4beds/2baths/huge backyard

MarkRating, 5 stars4 days ago
Place was great. Nice neighborhood. Extremely roomy home. Clean and nice kitchen and backyard for grilling/cooking. Will definitely keep in mind for next trip to Jacksonville. Highly recommend.
Guest favourite
Home in St. Augustine
4.95 out of 5 average rating, 99 reviews

new 4 bedroom home, 2 master-suites and pool

JoanneRating, 5 stars1 month ago
We had the best stay at Jody’s home! It was perfect for our group of 5 adults and 2 little ones. A quick walk to the beach and heated pool made for the perfect beach vacation! The home is beautiful.

Quick stats about house rentals in Fleming Island

  • Total rentals

    20 properties

  • Nightly prices starting at

    £30 before taxes and fees

  • Total number of reviews

    1K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Clay County
  5. Fleming Island
  6. House rentals