
Holiday rentals with a pool in Okaloosa Island
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Top-rated rentals with a pool in Okaloosa Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Okaloosa Island rentals with a pool
House rentals with a pool

Sugar Sand Cottage at Destin Pointe
Had an awesome stay at Sugar Sand Cottage with my family. The location is great and a short drive to various restaurants and activities. We loved the short walk (5 min) to the private beach with umbrella and chair service each day. The chair attendant had great local restaurant recommendations that we tried. The house is just like it’s shown in the pictures. We loved the layout with the porches overlooking the pond and private pool at night. Nichole was very responsive and can’t recommend this place enough. We will definitely stay here again when we come back to the Destin area.

Private Heated Pool! Walk 2 Beach!
We had a great stay in Destin! The house was clean and had everything we needed for a great beach vacation. The pool and back deck was a great place to enjoy coffee in the morning and dinner in the evening. Patrick was super responsive whenever I needed to contact him. The only negative was that the house is on a busy corner and with it comes a bit of street noise. I was pleasantly surprised however, that everyone slept great all 5 nights of our stay. Would not hesitate to stay here again!

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A
Our stay was amazing! The pool was a 10 out of 10 and well loved during our stay. The house was amazing and comfortable and offered our family the opportunity to spend some well needed quality time with one another. The house was also very nice and super clean.

Harbor Central Penthouse
This penthouse is exactly as listed- it is the most perfect location, just a simple step from the boardwalk, meaning all nightlife and restaurants are right at your doorstep. The dock right below the balcony allows for many activities such as renting pontoons to be just a step away. A 10 minute drive from beautiful beaches, and easy to get anywhere like target or stores, because it’s right on the highway. It was perfect for our large group of 7, and the apartment was super clean. Ryan is very responsive and a great host. Would recommend this Airbnb, and Destin, to anyone! (And the beds and pillows are incredibly comfy!!!!!!!)

#1 4BR HUGE PET Friendly Home w/ your own pool!
I highly recommend Anna house. She is such an amazing host and her home is perfect! Everything was very clean, comfortable & felt like home. We loved how spacious and big it was inside, we loved having the 4 restrooms. Everything was perfect! Anna was incredibly responsive and helpful. I would definitely book again.

Cozy Coastal Retreat | Near Destin &Okaloosa Beach
The house was more than just an AIR BNB, it was a Home! Gary and Tiffany provided a very clean and pristine home. They also provided amenities. The location of the home is close to the Harbor, Crab Island dock, Supermarkets, restaurants and more! the neighborhood was very comforting and welcoming. The home is perfect for couples, friends or family friendly get-away. I definitely recommend and will be booking with them in the near future!

Luxury 30A Cottage w/ Private Pool and Golf Cart
Adorable home situated in a secluded neighborhood with beautiful landscaping. The screened back porch was my favorite part of this home. The beds were very comfortable and I appreciated that this host ensures clean linens including a freshly washed comforter. You will not be disappointed.

Sunsail Cottage*Golf Cart Deals*Heated Pool Deals
Place was great the Pool was a good amenity, my five year old son love it. Very quiet peaceful neighborhood.
Apartment rentals with a pool

Gulf View Studio condo Fort Walton beach
Angelia was a fantastic host and the place was exactly how it was described and pictured. A perfect get away spot for a couple looking to relax on the beach.

Bluefish | Pool and Minutes Walk To The Beach!
Easy to get to and quick walk to the beach. Stewby’s is very close and great place to eat.

603 Destin West Gulfside - Amazing Penthouse View!
We've stayed in quite a few places along Okaloosa Island in the past. This one is by far the best. Check in was super easy a d Frank was available with answers. Highly recommend. Will book again.

Waterscape-Front Row Beach View - Great for Family
We visited with our two young children, and I was so pleased we did. The condo is right on the beach, which is beautiful. It came with an umbrella and two beach chairs, which were already set up! There was a great station for cleaning off the sand once we were done, and let us go directly to the pool. We loved it. The unit itself has a stunning view of the beach and the rooms are quiet and the kitchen and laundry was very easy to use. Take note: the kids bunk room does not have a closing door - just two swinging doors, so they can hear what is going on in the main area - but it is tucked away and our kids were so tired by the play, it wouldn’t have mattered. I would absolutely stay here again.

Gorgeous Penthouse w/ Ocean View, Huge Lagoon Pool
This condo was the perfect location for everything we where doing that week and the resort offered so much. Anytime I had question or concerns they where quick to respond and keep us informed. Would definitely book this Airbnb again!

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach
Our stay at the Oasis was amazing! It was very clean and organized. Everything was labeled and user friendly. Beach was within walking distance. Amado was very helpful and responsive, would definitely recommend this place to anyone!

Ocean Front, Corner Unit, Wi-Fi, 2BR, 2 BA
We've stayed at Connie's condo twice now and will stay again in the future! Breathtaking views and a comfortable environment that makes us feel right at home. Within walking distance of a convenience store and a couple local restaurants. Connie was accommodating and easy to communicate with. The photos of the unit and the photos of the views do not do them justice.

Dog-Friendly Coastal Getaway • Walk to Beach!
We had a great experience at this home. It worked well for the wedding venue we were in town for. House was as described and had everything you would need. It was clean and the communication was excellent! Thanks for a great stay!
Quick stats about holiday rentals with a pool in Okaloosa Island
Total rentals
2.4K properties
Nightly prices starting at
₹864 before taxes and fees
Total number of reviews
47K reviews
Family-friendly rentals
1.8K properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with dedicated workspaces
1.6K properties have a dedicated workspace
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- Destin Harbor Boardwalk
- Crab Island
- Princess Beach
- Frank Brown Park
- James Lee Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Shipwreck Island Waterpark
- Langdon Beach
- Grayton Beach State Park
- Blue Mountain Beach
- Pensacola Dog Beach
- Tiger Point Golf Club
- Pensacola Beach Crosswalk
- Camp Helen State Park
- Pensacola Dog Beach West
- San Carlos Beach
- Raven Golf Club
- Eglin Beach Park
- Gulfarium Marine Adventure Park
- Seacrest Beach
- Gulf World Marine Park
- Fort Walton Beach Golf Course
- Walton Dunes Beach Access