
Vacation rentals with a pool in Santa Rosa Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Santa Rosa Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Sea Oats*Beachfront View!2Bdr/2Bath, Sleeps 6
-Full beachfront view on the 4th floor with a balcony -2Bdr/2Bath: 1 king size, 2 twin size, 1 pull-out sofa-sleeps 6. 2 full bathrooms -Fully equipped kitchen -Free Wi-fi,Smart TV -Beach service (seasonal) -Outdoor swimming pool -Communal jacuzzi -Fresh linens,towels,essentials -Washer/Dryer -Grilling area -Communal workout room -Close to dining and shopping/peer -2 free parking spots -Close to Gulfarium -Close to Destin/Crab Island *By booking you agree to Short Term Property Rental Agreement

Destin West: Luxurious BAY View BEACH Access CONDO
Enjoy this luxurious 3bd/2ba 1,777 sq ft family friendly condo with a luxury master suite with Jacuzzi; & large balcony overlooking Choctawhatchee Bay. Walk to the dock & eat or sign up for a fishing charter, or rent your own jet skis or pontoon boat and make your way to Destin's Crab Island! Downstairs is the Lazy River, Waterfall pool, 2 heated pools, and 2 heated jet spas. Wristbands are required for this area. Guests can use the sky-bridge to access the beach, restaurants, and entertainment.

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!!

NAUTILUS 2608, Sleeps 6, Amazing Views!
Amazing views of the Gulf of Mexico from this 2 bedroom 2 bath condo, sleeps 6. On the 6h floor of the beautiful Nautilus condominium, you will enjoy the wide balcony with incredible views. Fully equipped kitchen, all linen and beach towels included. Beach service from March 1st until Oct 31st (2 chairs & an umbrella) Additional beach chairs and umbrellas in the condo. Heated pool. Many restaurants in the area. Groceries 5 min away. Special rates snowbirds and military on TDY. 25 yr old min.

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.

Condo With Serene Panoramic Views of the Gulf
This newly renovated 2nd floor condominium provides panoramic views in a serene atmosphere directly on the Gulf. This unit features a corner wraparound balcony with master and living room views of the emerald waters gently lapping at the white sand beach. This condo is on the quieter, more secluded end of Okaloosa Island just steps to a private beach. Two reserved beach chairs and service are included in your stay (March-October). Relax with the whole family at this peaceful place to stay.

Waterscape 3rd Floor 1 Bedroom - on the beach -
Bright and beautifully updated 1BR/2BA condo on the 3rd floor at Waterscape Resort with new flooring and cheerful coastal décor. The master features a king bed and en-suite bath, while kids love the bunk beds with TVs. Also includes a sofa bed, stainless steel appliances, in-unit washer/dryer, and beach chairs with umbrella stored in the unit. Enjoy partial ocean and courtyard views plus top resort amenities like pools, a lazy river, and a waterfall with easy beach and garage access.

Gulf Coast base w/ golf cart, patio & pool
Welcome to your Sandestin retreat - a peaceful Fairways townhouse where comfort meets coastal charm, just a short golf cart ride from the beach. - Sleeps 6 | 2 bedrooms | 3 beds | 2.5 baths - 6-seater golf cart included - beach & heated pools 5-7 mins away - Patio w/ fire table, BBQ grill & outdoor dining - Beach essentials provided - towels, umbrella & snorkeling gear - Washer/dryer on-site & self check-in via smart lock - Long-term stays welcome - snowbird pricing Nov-Feb

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.

Kid-friendly! Lazy River~Skywalk over to beach!
This is a beautiful one bedroom condo plus bunk area located on Bayside of Destin West! The unit comes equipped with a beach cart to make the short walk to the beach even easier! You will love the location of this unit! Freshly painted, with beautifully decor, plus beach towels (2) - you will feel right at home at our 'Salty sandpiper'. With a fully stocked kitchen, washer and dryer, and a lazy river pool - this condo is the perfect place for your beach getaway!

Island Princess 618 | Beach Service Included
Experience the perfect beach escape in our beautifully renovated beachfront condo on stunning Okaloosa Island. This inviting retreat offers two spacious bedrooms, two modern bathrooms, and a rare oversized balcony—ideal for relaxing while taking in breathtaking Gulf views. Step onto the sugar-white sands and enjoy the emerald-green waters with complimentary beach service, including two chairs and an umbrella, provided from March 1 through October 31.

607 Destin West Resort - Gulfside Penthouse View!
Welcome to Destin West Gulfside #607! I'm Frank, your host for this great vacation property. This very nice beach condo is a 1 bedroom + 1 bunk room and 2 full bath. With the sleeper sofa in living room the property sleeps up to 6 guests. The Resort includes direct beach access, many pools, and a lazy river. Additionally, the beach service is included for free (2 chairs/ 1 umbrella)! (*Please review entire 'House Rules' section before booking.)
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Emerald Coast Escape

Sugar Sand Cottage at Destin Pointe

Its 5 o'clock here

Waterview Villa, Steps to the Sand, King Bed, Pool

Emerald Oasis: Hot Tub + Sleeps 18 + Pool+ Grill

Harbor Central Penthouse

#1 4BR HUGE PET Friendly Home Away from Snow!

Relaxing Pool Retreat Near Beaches & Destin!
Condo rentals with a pool

3BR ~ Beachfront ~ Huge Balcony ~ 2 Pools ~ Luxury

Keeler Island Princess #508 Okaloosa Island Bchfrt

Veranda 102 - Direct Beachfront - Gulf Side Pool

Destin West V409 Cozy Beach Getaway 7Amazing Pools

Beachfront END UNIT+Beach Serv- Lazy River-7 Pools

"SeaGlass" - Oceanfront with expansive balcony.

Penthouse-Huge Roof Top Patio w/ Hot Tub-LazyRiver

2 Bedroom Condo on the Beach at Okaloosa Island
Other vacation rentals with a pool

Stunning Soundfront 2BR: Easy Beach Access & Views

Beautifully Updated Beachfront-Free Beach Service!

Pool Table, Lazy River, & HUGE Patio! Destin West!

Gulf Views • Beach Service • Steps to the Beach +

Unit #5 Waterfront + Heated Pool and Spa Access

WaterScape Now Booking 2026! Beach/resort/pool/spa

Gulf Front | Spacious Condo | Water Views | Pool

Island Princess 301 - No Shoes Retreat-Gulf Views
When is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$33,898 GYD | G$38,293 GYD | G$46,872 GYD | G$47,081 GYD | G$48,127 GYD | G$59,636 GYD | G$63,821 GYD | G$44,989 GYD | G$39,757 GYD | G$38,502 GYD | G$34,526 GYD | G$33,689 GYD |
| Avg. temp | 12°C | 14°C | 17°C | 20°C | 24°C | 28°C | 29°C | 28°C | 27°C | 22°C | 16°C | 13°C |
Quick stats about vacation rentals with a pool in Santa Rosa Island

Total vacation rentals
Explore 2,670 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at G$14,647 GYD per night before taxes and fees

Verified guest reviews
Over 52,240 verified reviews to help you choose

Family-friendly vacation rentals
2,020 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
1,560 properties have a dedicated workspace

Wi-Fi availability
2,660 of Santa Rosa Island vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Santa Rosa Island rentals

4.7 Average rating
Santa Rosa Island stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Santa Rosa Island's top spots, include Destin Harbor Boardwalk, Gulfarium Marine Adventure Park, and Crab Island
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- Rentals with pools Okaloosa County
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- Rentals with pools United States
- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Frank Brown Park
- Henderson Beach State Park
- Seacrest Beach
- Navarre Beach Fishing Pier
- Village of Baytowne Wharf
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Aqua Resort
- Grayton Beach State Park
- HarborWalk Village
- Gulf Breeze Zoo
- Topsail Hill Preserve State Park
- Pier Park
- Jade East Towers
- Fort Walton Beach Landing
- The Boardwalk on Okaloosa Island
- Shipwreck Island Waterpark
- Camp Helen State Park
- Gulf World Marine Park
- Gulfarium Marine Adventure Park





