Holiday rentals with a pool in Okaloosa County

A light-filled living area features a comfortable sofa facing large glass doors that open to a private balcony, revealing sweeping views of the Gulf of Mexico. A wooden dining table is set, accompanied by modern white chairs. A unique chandelier hangs above, adding contemporary style.

4.96 out of 5 average rating, 231 reviews

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.

Apartment in Fort Walton Beach

4.98 out of 5 average rating, 122 reviews

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!!

A comfortable living area is highlighted by an overhead ceiling fan and a wall-mounted TV. Large glass doors provide a view of the Gulf, leading to a private balcony furnished with seating. Light curtains frame the windows, allowing natural light to fill the space.

5 out of 5 average rating, 114 reviews

1203 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 1203—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 12th 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.

4.94 out of 5 average rating, 154 reviews

A private backyard area features a heated plunge pool surrounded by palm trees and landscaped rock beds. Comfortable seating options include Adirondack chairs and a fire pit nearby. A grill is available for outdoor cooking, creating a relaxed environment for gatherings.

Home in Destin

3BR Crystal Beach Retreat | Pool + Walk to Beach

Whether chasing sunsets, grilling out, or splashing in the pool, we offer the perfect mix of comfort, convenience, and coastal charm for your vacay. 📍 LOCATION ✦5-min walk to TWO beach accesses ✦Close to Destin Commons ✦Quiet street with a laid-back beach vibe ✔3 Bedrooms ✔Private Plunge Pool ✔323 Steps To The Beach ✔Fenced Backyard ✔Fire Pit + Park Style Grill ✔Smart TVs In All Rooms ✔Digital Game Table ✔Beach Wagon + Beach Chairs (4) ✔Easy Parking + Unloading ✔1100 sq. ft Open Floor Plan

4.97 out of 5 average rating, 394 reviews

An outdoor area features a private pool surrounded by a patio with lounge chairs and a dining table. Two surfboards are positioned near the pool, alongside palm trees and residential buildings in the background, creating a relaxed, tropical setting.

Guest house in Destin

Carriage House by the Beach

Cozy carriage house one block from the most beautiful beaches in Florida! Enjoy a full kitchen with granite counter tops and all of the tools needed to cook a fantastic dinner to eat on your deck overlooking the pool. Snuggle on the couch watching a large TV or catch up on social media with free Wifi. Sleep in a comfortable king bed and enjoy a private bath. Walk to restaurants, shops and nightlife. Perfect for a vacationing couple or anyone in town for business. Includes beach chairs!

Apartment in Fort Walton Beach

A serene twilight view captures the sky filled with clouds reflecting subtle shades of orange and blue. The marina lights twinkle along the water's edge, while the horizon highlights an array of colors as day transitions into night.

4.97 out of 5 average rating, 197 reviews

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.

An aerial view captures the resort layout amidst lush greenery, showcasing the expansive lagoon pool at its center, surrounded by sun loungers. In the distance, the coastline of the Gulf of Mexico glistens under bright sunlight, with buildings lining the beachfront.

4.96 out of 5 average rating, 163 reviews

Gulf View. Pool open until 11:00pm! Walk to beach.

2BR/2BA is located on the 6th floor condo at The Palms of Destin Resort. Views of Henderson State Beach across street. The master has a king size bed and bathroom. Twin trundle beds in small bedroom and bath. The living room has a queen sleeper sofa & 80" TV. The lagoon pool, heated pool, and hot tub is open until 11pm. Amenities include a gym, basketball, tennis, splash pad, arcade, and playground. Dollar Tree, Walmart, Enterprise Car Rental next door. Walk to restaurants and 2 beaches.

Guest house in Fort Walton Beach

A spacious outdoor area features a blue umbrella over a dining table, adjacent to a clear swimming pool. Lush greenery surrounds the pool deck, with views of the tranquil water in the background. The scene is complemented by palm trees and a well-maintained lawn.

4.84 out of 5 average rating, 191 reviews

Private Guest House on the Water | Boat Docks!

You’re invited to enjoy the breathtaking panoramic views as you start your day on our private waterfront deck. This lovely beach house offers one queen bed in the bedroom, a twin/full bunk bed, and the sofa in the living room is a pull-out queen bed. Full-size kitchen and dining area. Dock your boat in a private boat slip for a small daily fee. ✔ OMG Views ✯ Waterfront ✯ Private Beach ✯ Entire Place ✯ Boat Slips ✯ Trailer parking ✯ 2 Story Dock ✔ Dog friendly ✔ Full Kitchen ✔ 2 x Smart TV

4.92 out of 5 average rating, 186 reviews

Flat in Destin

Luxview

The Luxview was completely remodeled with a special attention to detail to make your stay exclusive. The warm and welcoming atmosphere is ideal for couples romantic gateway. Located in the HEART of Destin, within 2 minutes drive to the stunning beaches. The complex has 3 pools, a lake and a tennis court. Ideally located, you can walk to restaurants, shopping or to Big Kahuna's Water Park. Enjoy coffee and breakfast at sunrise or have a drink outside at night on the nice lakeview balcony.

4.96 out of 5 average rating, 133 reviews

The beach cottage features a welcoming exterior framed by palm trees and tropical foliage. A white picket fence surrounds the property, leading to a spacious porch with multiple steps. The home’s two levels and large windows create an open and airy appearance.

Home in Destin

Sugar Sand Cottage at Destin Pointe

This beautiful four bedroom beach cottage is located in the exclusive gated community of Destin Pointe. The home offers a tranquil setting and unsurpassed amenities that include a private lakefront pool for relaxation and entertainment-perfect for sipping your evening cocktails while overlooking the lake, direct lake views for the multiple levels of decks, private beach access to the sugar sands of Destin, and three community pools (one with a hot tub and splash pad) for guests use.

The living area features comfortable seating arrangements, including a spacious sofa and armchair. A coffee table sits in front of the television, which displays a coastal scene. Large windows framed by sheer curtains allow natural light to brighten the room while offering views of the outdoors.

4.83 out of 5 average rating, 121 reviews

Luxury Destin 1BR Jetty East Beach Resort Condo

Discover a tranquil retreat at Jetty's East in Destin, Florida. Unit 104A is a charming 1-bedroom condo located within this beachfront complex. Enjoy direct beach access just steps away. Relax in the comfortable living area, prepare meals in the fully equipped kitchen, and unwind in the cozy bedroom. Take advantage of the resort amenities, including a pool, hot tub, tennis courts, and fitness center. Explore nearby attractions, shops, and restaurants for a delightful beach getaway.