Holiday rentals with a pool in Crestview

The Merry Whale on The Emerald Coast

Newly updated 1 bedroom/ 2 bath condo with built in bunkbeds. Located beach side on the 19th floor with breathtaking panoramic views of the emerald waters and pristine white sand beaches The Gulf of Mexico. Fully stocked kitchen with new granite countertops and slate appliances. Reliable fast high speed internet throughout. Resort amenities include a large pool and hot tub, a beachside tiki bar serving frozen drinks and beer. A fabulous cafe that serves hot breakfast, pizza, sandwiches & salads.

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA

Islander Beach Resort is a 7-story structure of 114 condos on a short 2 mile stretch of Okaloosa Island and sits DIRECTLY on the BEACH. The building is painted aqua blue and gray, and all units overlook the ocean. There are 2 elevators and lots of parking. Guests can freely access the beach, HEATED pool, BBQ pits and parking area (a parking pass is needed from lobby). You will probably spend a lot of your time on our large private balcony overlooking the pool and beach, listening to the waves.

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!!

The 30A Beach House | Private Beach + Dune Pool

Welcome to The 30A Beach House, a fully renovated coastal home, inside a private gated community between Rosemary and Alys Beach What Guests Love • 2 bedrooms | 2 bathrooms | sleeps 6 • Private deeded beach access 1-2 min walk • Heated pool on the dunes with Gulf views • Walkable & bikeable to Rosemary & Alys Beach • 4 complimentary cruiser bikes, professionally maintained • Fully stocked beach setup (chairs, umbrella, cooler, toys) • 500+ Mbps WiFi • Dog-friendly • Rare Two-car garage parking

East Bay Hideaway — A Private Waterfront Escape

Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

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.

Waterfront Studio • Santa Rosa Sound • Sunsets

Enjoy breathtaking views of the Santa Rosa Sound and marina from your private top-floor balcony in this waterfront studio. Whether you're sipping coffee at sunrise or watching vibrant sunsets each evening, this spot delivers unforgettable costal charm in a quiet, peaceful setting. Perfect for couples or solo travelers, the studio features a full bath with tile shower, well-equipped kitchenette and sparkling pool. Gulf beaches are a just a short drive away. Free parking and easy self check-in.

Luxury 30A Cottage w/ Private Pool and Golf Cart

A NEWLY BUILT LUXURY COTTAGE DESIGN BEACH HOUSE WITH PRIVATE/HEATED POOL* AND GOLF CART in the heart of Santa Rosa Beach off 30A. This beach house is nestled among the trees yet only minutes away from the white sandy beaches. Bask in the sun by day and wind down and relax in the outdoor areas surrounded by a peaceful wooded area by night. It is like stepping out of one world directly into another. Come and Relax and enjoy the peace and tranquility of this cozy retreat.

Our Happy Place

Pack your bags and head to Our Happy Place. Readily equipped with everything you will need for relaxation, fun or adventure. Our Happy Place is situated on the water where you can sit and watch boats go by, or fish from the shore. Take a dip in the community pool that offers plenty of lounger chairs and tables with umbrellas. Just across the street you will find a boardwalk to stoll down to the white sandy beaches where you can soak up the sun and Gulf of Mexico views.

100 ft to sand, Corner unit, Hot Tub, Garden view

Step out and hit the beach—just 100 ft to the sugar sand beach from this charming condo. Featuring a King master suite w/private bath, 2nd King room, plus a bunk-bed cubby for kids with a hall shared bath. Ground level, corner unit. The fully stocked kitchen includes Keurig w/pods. 3 TVs. Private patio. Just steps from pool & hot tub. Wi-Fi, washer/dryer w/starter pods. Stroll to dining and local attractions. 2 FREE parking spots. Rent 25+ unless active duty military.

Soundside Paradise

Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!

Stars & Sea•Overlooking Pool & Sound•Sleeps 4

Kick back & relax in this calm, newly renovated ground-level condo on the Sound in Ft Walton Beach! ✨ Highlights: • 🌴 Waterfront views & stunning sunsets • 💦 Large resort-style pool • 🏖️ Minutes to beach access • 🍽️ Walk to local restaurants • 🚗 Easy parking & quiet community 🛏️ Queen bed w/Purple® mattress + Queen memory-foam sofa bed ☕ Kitchenette: Fridge • Air fryer/toaster • Microwave • Keurig •7.5 Miles to Destin