
Holiday rentals with a pool in Crestview
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Top-rated rentals with a pool in Crestview
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Popular amenities for Crestview rentals with a pool
House rentals with a pool

Beautiful Paradise Home - 1 Mile From Beach - POOL
Jake’s home was spacious & in a very great location — close to restaurants, beach, & private neighborhood. I would recommend this home to anyone looking to stay in the Perdido Key area.

Tranquil home in Bluewater Bay
This home was absolutely perfect for our group of 8! The pictures don’t do it justice — it’s even more beautiful and spacious in person. We were welcomed with cookies and wine, which was such a thoughtful touch. The house was spotless, stylish, and had everything we needed. The pool area was clean, private, and perfect for relaxing but it could use a little update. Great location too — peaceful but close to beaches and restaurants. The hosts were fantastic and made everything easy. We’re already planning to come back! Thank you!!

1.5 mi to Beach-New Pool! Smart home-Modern Decor!
Joey was an outstanding host from start to finish. His hospitality and attention to detail truly set this stay apart. From the moment I arrived, it was clear that he put a lot of thought into making the space welcoming and comfortable. There were so many thoughtful touches throughout the home that made me feel right at ease. The place itself was spotless, beautifully maintained, and had a very relaxing atmosphere. It was the perfect getaway spot. The bed was incredibly comfortable, and everything I needed was readily available. One of the biggest highlights was the pool—it was absolutely amazing. Clean, private, and perfect for lounging or taking a dip to unwind. Joey really went above and beyond to ensure my stay was enjoyable. Communication was quick and helpful, and he made sure I had everything I needed. I’ve stayed in quite a few Airbnbs, and this experience ranks at the top. Five stars all the way—I would absolutely stay here again and highly recommend it to anyone looking for

Good times & tan lines! Only 5 miles to the beach!
This is our 3rd stay at Juan’s place, and 10/10 always a 5 star review!! Plenty of space, clean, always responsive to any questions we have. The kids love the back porch area and swimming pool, the pups love the yard! All the beach amenities you can imagine in the garage. Wonderful place, with matching hosts!

North End Retreat | 3 Bed 2 Bath
Great place with a responsive host. Home was close enough to everything we had planned. Pool was definitely our favorite part. And although it rained the entire weekend, we enjoyed our stay. Very accommodating. Would book again.

The Charleston Experience-Free PoolHeat N GolfCart
We had a fantastic stay at this charming cottage in Destin! The location couldn’t be better—just a short walk or quick golf cart ride to the beach, great restaurants, and shopping. The house was spotless, tastefully decorated, and felt like a true getaway. We especially loved having access to the golf cart and relaxing by the pool after a day in the sun. Highly recommend this place for anyone looking for a cozy, convenient beach vacation!

Soundside Paradise
Robert’s place was extremely clean and really nice. We really enjoyed our weekend and would definitely stay there again.

4 bd/rm, 15 min to beach & private pool
Went for a girls trip and loved this place! None of us had kids but they have toys and so much more for children if you are bringing them! Everything we did out in town was not far either!
Condo rentals with a pool

Discounts|Steps to Beach|Pool|Tennis|Hot Tub
This condo is so close to the beach. We used the beach umbrella and chairs that were provided by the host. But for $30 there is a beach service that will set up chairs for you. We stayed here with two kids. We enjoyed the pool and pickle ball courts as well. I booked this condo last minute because our original place cancelled unexpectedly. I was a little disappointed by the view when I arrived because the bay is pretty far away and our original place had a ocean view. On our last night we were surprised by a firework show on the bay. You could not ask for a better view of the fireworks. It was the perfect way to top off our trip. Tip: Walk to the jetty and take a right. Keep walking till you get to the next beach. That is where boats take their guests for snorkeling tours. So many fish and a great place for kids as long as you don't go out too far because it gets deep quickly.

Perfect View on Santa Rosa Sound with 2 Pools!
Randy’s condo was an amazing find and the perfect place to relax for the weekend. Would recommend staying here!

Gone Coastal 0.8 miles to beach, monthly discount
Great place!!! Very clean and good area!!! Really enjoyed our stay!!!!!

Splash Resort~1906E~Best in PCB~Free Beach Chairs
This Airbnb matched the description, had all the listed amenities, and was so clean and nice that I had no worries like I would in a hotel! The view was BEAUTIFUL, the balcony was large and we liked that we could access it from both living room and bedroom, and overall an amazing place! It was also great since we had two young kids. The kids room was perfect and my daughter loved it. Also, the crib was SO nice as most places don't have that! Five out of five stars for both the place and the owner as they were available and quickly responded to our questions and checked in on us!

Lovely beach-front condo with free beach setup.
The condo was the best we have stayed in. The furniture upgrades both inside and out were a nice unexpected surprise as they weren’t shown in the booking photos. The bed might be the most comfortable ever made! My only complaint, and it’s not really a complaint, is the beach service is a little confusing. You do get chairs and umbrella included but to insure a front row you need to be on the beach early and talking with the guy putting out the chairs about securing some, it’s first come first serve on ones that aren’t reserved. You can also pay $15.00 extra a day to reserve a set. The beach service guy was awesome and took great care of us all week. Highly recommended! Oh, and the pool was not heated and in first of May was a little cool but certainly is of no fault of the owner.

Beachfront 8th Fl. 1 BR at Pelican, Stunning Views
My husband and I had a great time in Destin and this unit was perfect for what we needed! We loved that the balcony gets shade most of the day so we could sit out there and not be burning up. We loved how many restaurants and activities there were to do around the area. Very communicative and checked in on us when we arrived. Definitely recommend!

Lochshire: 30A Escape! 2BR-Beach-Pool-Cart-Fun!
We had a marvelous stay! The location was right in the center of all the hot spots, and the amenities were fantastic! We loved riding around in the golf cart! For our first stay in Rosemary beach, the guidebook was fantastic at directing us to everything we needed to know! We will definitely be back!

Sunshine and beach time /Okaloosa Island
Me and my family had a great week in David and Carons condo! They were attentive, gave me and my family a few things to do while we were vacationing. I will definitely get this place again.
Home rentals with a private pool

7BDR w/ Pool+Hot Tub, Walk to Beach | Tidal Wave
Our family reunion could not have been better as we enjoyed the Destin area for the first time. The home was perfect for four adult couples and five grandchildren. Access to the Tarpon beach was easy. The swimming pool offered hours of fun. The kitchen was well supplied as we prepared numerous meals for all 13 of us. When we had any issues, the responses were immediate and successful - to include a new coffee pot when the old one suddenly stopped working, two new portable air conditioner units when one of the 3 major a/c systems stopped working, and extra bath towels and wash cloths for the bathrooms. And the weather was perfect - temperatures in the high 70’s to low 80’s and relatively low humidity - and no rain during the day! One suggestion for the crew coming in to clean the house after a stay would be to wet-mop the dark hardwood floors. All in all - a wonderful vacation in a terrific home. Gary & family

18occ! Pool + Walk to Beach | Miramar Beach Jewel
The house was perfect! All our guest were pleased and plenty of room. We had 16 to stay and no one had any complaints. Great time and highly recommended.

Bayou Breeze
The place was very nice and clean. The hostess was very nice and responsive. The only thing I wish I would have paid more attention to was the heated pool. The temperatures were cooler than usual, so the heater wouldn't keep up. We paid to heat it but it was always too cold to swim.

Sleeps 18! Pool, Near Beach | Miramar Dream House
Great for large group to spread-out. Bedrooms are all roomy. Quick walk to the beach or drive to public parking. Well equipped kitchen.

Villa Near Beach w/ Pool + Hot Tub | Woodward Way
Wonderful location near the beach and tons of restaurants. We loved cooking in the specious kitchen and hanging by the pool.

Coastal Retreat

New! Salty Sue
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- Destin Harbor Boardwalk
- Crab Island
- Princess Beach
- James Lee Beach
- Navarre Beach Fishing Pier
- Grayton Beach State Park
- Blue Mountain Beach
- Pensacola Dog Beach
- Pensacola Beach Crosswalk
- Tiger Point Golf Club
- Gulfarium Marine Adventure Park
- Camp Helen State Park
- Raven Golf Club
- Pensacola Dog Beach West
- Seacrest Beach
- Eglin Beach Park
- Fort Walton Beach Golf Course
- Wayside Park, Okaloosa Island
- Walton Dunes Beach Access
- Osceola Municipal Golf Course
- Gulf Breeze Zoo
- The Track - Destin
- Eglin Matterhorn Beach Access Point
- Fred Gannon Rocky Bayou State Park