Holiday rentals with a pool in Crestview

Beach Penthouse on Okaloosa Island in FWB, FL

Unit 301 has the best views being it is an end unit on the top floor. It also feels very spacious with its vaulted ceilings and unique loft area. Sleeps up to 6 people. Queen bed in Master. Another Queen bed and bath in loft. One full size sleeper sofa in living room. Owners have used the unit for past 9 years and have just decided to offer it as a rental. Freshly painted, and updated with new carpets, floors, furniture and appliances. Unit has everything you need for a wonderful vacation.

East Bay Getaway - Studio with Pool & Hot Tub

Welcome to East Bay Getaway, a private studio nestled in the woods. This clean and comfortable room with private entrance is a MIL suite attached to your host's home, on more than an acre. It features a kitchenette (no stove), high-speed WiFi, 32" smart TV, and dedicated HVAC system. Plenty of outdoor space, with a large pool and hot tub in the shared, privacy fenced backyard. A bike/walk path is directly across the street, which goes for miles either direction. 3- burner BBQ grill - NEW for 25!

Beachfront Bliss! Gulf Waves at The Palms #201

Nestled on shimmering Gulf shores, The Palms #201 invites you to unwind with jaw-dropping oceanfront views. This 2-bed, 2-bath sanctuary is your ticket to an unforgettable coastal retreat. Steps from the water, this guest favorite blends relaxation and rejuvenation for a home-away-from-home feel. From March through October, we provide complimentary beach service with two chairs and umbrella—a $40 daily value included free! Pure paradise is at your doorstep. Book this dream coastal escape today!!

1004 Oceanfront Pelican Beach: Pools/HTubs Fab Loc

NO PETS PERMITTED. PRIMARY GUEST MUST BE 25+ TO BOOK. Indulge in a refined coastal escape at Pelican Beach Resort 1004—an elegantly renovated 1‑bedroom, 2‑bath BEACHFRONT retreat offering breathtaking Gulf of Mexico views and DIRECT, effortless access to Destin’s sugar‑white sands. Perched on the 10th floor, this beautifully appointed residence blends contemporary comfort with resort‑level amenities for UP TO 6 GUESTS, creating an elevated experience for both families & discerning travelers.

Kokomo Key on Navarre Beach - Private Pool

If you've been searching for Kokomo Key... Here it is—your tropical escape to the islands 🌴. White sand, turquoise waters… it’s got all the vibes of a place where time slows down and the only agenda is relaxation. Relax with the whole family at this peaceful beach house with a private pool, hammocks, unobstructed views of Santa Rosa Sound, and a 2-minute walk to the stunning Gulf beaches! We are pet friendly, but please remember to let us know you are bringing your pets by checking the box!

Regency end unit, discounted fall/winter rates!

We've gone to great lengths with extensive recent renovations to make our condo feel like a full 5-star experience - just read the reviews! There are several things that set our unit apart from others, most notably the incredible views in two directions! Add in beach chair service (March through October), along with new appliances and other renovations that are too numerous to list fully, and you have one of the best beach vacation experiences imaginable without spending a small fortune!

PrivatePool/Oasis/WholeHouse/nearBeachesDestinFWB

Conveniently located in North Crestview, our home provides a perfect base for all that Northwest Florida has to offer. From beaches to rivers to the refreshing pool & huge backyard, your vacation options are endless! The neighborhood is peaceful and quiet. It’s a perfect place to enjoy a long walk or run, lounge by the pool (with excellent privacy fence!), grill out for dinner, or use as a home base to explore the area. We are conveniently located less than 40miles from Destin beaches.

Destin West V409 Cozy Beach Getaway 7Amazing Pools

Newly updated modern beach-side unit. Luxurious renovated bathroom. This Gulfside unit is steps away from the white sandy beach, 7 different pools, and many restaurants. Located on the 4th-floor with one of the best views in the Florida panhandle. A 180-degree view of the emerald waters of the Gulf of Mexico, Choctawhatchee Bay, the Okaloosa Island sand dunes, and the Destin city-scape. Relax in the lazy river pool, sunbathe at the beach, or spend your day being adventurous.

Carriage House 1.5 bed/1 bath located off 30A

You’ll love our place because of the ambiance, the neighborhood, the people and the location. This guest house is located in a gated community just steps from the beach with a community pool across from the home. Beach is 700 steps from front door along a paved sidewalk to private beach access for the neighborhood. The Carriage House is perfect for couples, families (with kids), and solo adventurers. Need more room? We have a larger home on property that sleeps 11.

CasaBonita-Sandestin® 2BR/3BA/Loft-Cart to Beach!

Escape to CasaBonita, a stunning 2BR+Loft/2.5BA villa on Sandestin®’s Raven Golf Course. Sleep up to 7 with sweeping lake and golf views, enjoy a private patio, and explore with a 2024 6-seater golf cart. Access private beaches, pools, tennis, spa, and Grand Boulevard. Walk to Baytowne Wharf for dining, shopping, and fun. Luxury, adventure, and coastal charm blend perfectly for your unforgettable Sandestin® getaway. Book now and start your dream vacation!

Private Beach! Ground Floor Condo & Beach Service

Let Your Vacation Begin! Walking on the Stunning Sugar White Sand, surrounded by the Turquoise Water, you will be transported to the World of Relaxation! Perfect for Couples or Family Getaway! Destin Beaches have won National Awards for the "Cleanest Beaches" Luckiest Fishing Village" In addition, several Beautiful & Challenging Golf Courses! Harbor Walk Village, Largest Fishing Fleet in the Country! Buccaneer Pirate Cruise FUN!!!

Spacious 4BR Oasis w/Pool Hot Tub & 2Master Suites

Unwind in style at this beautiful 4-bedroom, 3-bath retreat featuring two luxurious master suites—perfect for families or groups. Enjoy a sparkling private pool, relaxing hot tub, and cozy living spaces designed for comfort. Whether you're soaking up the sun, cooking in the fully equipped kitchen, or winding down in one of the spacious suites, this home is your ideal getaway.