
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

Poolside Paradise! Book your ‘25 Getaway!
Beautiful house, in front of the pool, feels like your at home. You have everything for your stay. Perfect for my guests.Very clean & spacious . We have some much fun.

Private Pool! 0.7 miles from Beach & Restaurants!
Thoroughly enjoyed our stay! Located close by the beach with a beautiful view. Will definitely be returning soon

~Private Pool ~ Walk to beach and shops
Can’t say enough great things about this place! The house was extremely comfortable for two families with little kiddos. I also considered renting it in the future for a girls trip! Such a great set up. The house was comfy (especially the beds! So comfy!), location was AMAZING, and the host was super helpful. The house was even better than the photos. We walked to so many great places. Great little paths for running in the morning as well. I would 100% recommend this to friends and family in the future if heading to a trip on the beaches of 30-A!

Great 3 Bedroom home in Crystal Beach! Private
What an amazing place! Our family had the best time ever. I can't recommend it enough!

Beach, Hot Tub, Huge Pool / Yard, and Dog friendly
We really enjoyed staying in her home. She was very welcoming and very responsive to anything we needed. She also made sure to check in and see if there was anything else we needed. We would recommend her and use her again. Thanks again

#1 4BR HUGE PET Friendly Home w/ your own pool!
Loved this house so much! The family had a great time and their pool is so big and nice! Very quiet neighborhood! Will definitely stay again! Anna was very helpful.

Malibu Chic Home w/ Carriage House & Pool!
This house was amazing for our bachelorette weekend! The house was clean and beautiful and everything was as advertised. The house is located on a quiet street but still very close to great restaurants and walking distance to the beach! Emily was a very responsive host when we had a question, and provided local recommendations for golf cart rentals and restaurants. We loved this house!!!

Salt Therapy *BBQ *Enjoy a Private Pool & Hot Tub
Great place! Our family really enjoyed our stay. The backyard was private and great for us and our Westie. Spacious rooms with comfortable beds and other very nice furniture throughout the home. The kitchen was well stocked with cookware and utensils to prepare meals. The entire property, inside and out, was updated, neat, clean, and well maintained. Amy was a great host, very responsive. Definitely recommend this home and host!
Apartment rentals with a pool

Gorgeous 3 bed 2 bath condo with pool near beach
George was an awesome host!! One minor thing was broke, and I bought it to his attention he came in fixed it in 10 min or even less!!! His place was cozy, clean, and neat most definitely the perfect location less than 5-10 min drive to all the places we was going to for our vacation with the kids.

Destin beaches at an affordable rate
I only have amazing things to say about this stay. It might be my favorite place I’ve ever stayed-truly feels like a home away from home.

Pool |150 Steps Beach|Sleeps 6|Public Beach Access
Cute, comfy and quaint! The place looked exactly like the photos. The heated pool was just a few steps away in the backyard, the beach was just right across the street and there were great restaurants in the area. Our host Jonathan was very accommodating. Everything we needed was provided, clean wash cloths and towels, cookware and utensils, even beach toys. The only complaint if I had to make one were the loud footsteps from the neighbors above us, other than that it was perfect for our mini vacation. We really enjoyed our stay and we’ll be back!

Gulf Front Condo - with heated Pool
5 stars all the way for what we were looking for: a great location, on the beach with a beautiful view. I'm not sure there is another place that could deliver on the level this condo did for all those features. As a host, Dave was proactive on checking in on us to make sure everything was going smoothly and was ready to respond if we needed anything. Also appreciated the value and flexible cancellation policy. However, one caveat: there were few small things detracted slightly from our stay (but not enough to take away a star). Just some small things. We received additional "instructions" or chores that were not included in the listing. Dump the water from three dehumidifiers (which are loud, run constantly and blow out warm air) daily or the AC will shut down. Upon leaving, do the dishes, take out the trash, remove all linens and put them by the washer (all of which we did). $300 cleaning fee for?... Also, a request to "leave a 5 star review because anything less is a 'bad review'".

Palm Paradise*Destin Harbor Condo*
My family of 5 thoroughly enjoyed our stay! The apartment was thoroughly clean, beautifully furnished, and in a picturesque and private area. The beautiful beach was within walking distance and the pool was directly downstairs. We highly recommend Oana’s Destin getaway!

The Palms of Destin- Spectacular lagoon pool! 2610
The Condo is very comfortable, clean, it has everything you might need, very nice decorated, I love it. thank you so much. Excelente lugar, super limpio y tiene todo lo que una familia necesita. Gracias.

Condo-B, steps to beach, pool, sleeps 4+, king bed
Had a great weekend trip! Condo was clean and comfortable!

Lakefront Condo steps away from the beach
It was all about the location-lakefront and walkability for me...a quick walk to the beach, Whale's Tail for fresh blackened grouper, Kilwin's overpriced but def worth it, ice cream, BadAss Coffee shop. The condo is in the gated Seascape resort which felt safe. I really enjoyed the screened in porch, lakefront view every am. Maria also provided beach towels and beach chairs. It could def be updated - bed covers reminded me of a motel and could use room darkening curtains, as the outside light is bright. I could hear people in the above units walking and entering at 11pm (at no fault of the hostess's). Overall, Maria was a responsive and accommodating hostess (when I wanted to check-in early). It was a spontaneous and relaxing spring break trip for me and my pup and loved how close I was to the beach WITH lake views. I appreciated that the condo was managed by Maria and not a rental company that has high cleaning charges and pet fees.
Home rentals with a private pool

7BDR w/ Pool+Hot Tub, Walk to Beach | Tidal Wave
Stayed here for my bachelorette party and it was perfect for everyone. The outdoor area was nice and big for our group. The host was extremely responsive. There is a $150 early check in fee if you want to do that. Would definitely recommend this place to others!

Sleeps 18! Pool, Near Beach | Miramar Dream House
Wonderful host, everything was described. Plenty of towels and wash rags in every bathroom and towels for the pool too was very convenient for my large group. We had an issue with the hot tub (at no fault to the hosts- the kids left the cover off over night causing it to cool all the way off) but when I reached out to them they had someone there so fast like within 20 mins or so. Would recommend them 1000%.

Villa Near Beach w/ Pool + Hot Tub | Woodward Way
There were 9 of us staying here and it was a great amount of space! We loved how close we were to the beach and quick drive to many local areas. The host was able to accommodate an early check in and was very responsive and helpful during our stay. We enjoyed our stay and recommend to anyone coming to Destin!

Near Beach, Private Pool | Bohemian Beach Retreat
The AvantStay team was amazing. We had questions and requests and each time they did everything they could to accommodate our needs. They went above and beyond at times and made us feel like valued customers. The house was fantastic, we had a party of 10 and it was perfect. Everything about the house: the pool, the location, the hot tub, exceeded our expectations. We would definitely stay again and would use AvantStay as well.
Quick stats about holiday rentals with a pool in Okaloosa Island
Total rentals
2.4K properties
Nightly prices starting at
£8 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
- James Lee Beach
- Frank Brown Park
- Princess Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Shipwreck Island Waterpark
- Blue Mountain Beach
- Grayton Beach State Park
- Langdon Beach
- Pensacola Beach Crosswalk
- Tiger Point Golf Club
- Raven Golf Club
- Gulfarium Marine Adventure Park
- Pensacola Dog Beach
- Walton Dunes Beach Access
- Eglin Beach Park
- Pensacola Dog Beach West
- San Carlos Beach
- Osceola Municipal Golf Course
- Seacrest Beach
- The Track - Destin
- Eglin Matterhorn Beach Access Point