
Vacation rentals with a pool in Santa Rosa Island
Find and book unique homes with a pool on Airbnb
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$14,638 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
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!!

Beach Side- 2Br 2Ba 3bed | POOLS- GEM-BEACH!
Walk to the Beach at Sunset or Sunrise Every Day! 2 pools, indoor pool & outdoor pool next to the White Sand Beach Access, BBQ Area, elevator & fitness room amenity. Come and enjoy Fun & Sun at our condo by the beach! Gorgeous 2 Br 2 Ba condo is an amazingly nice & quiet like open air community on 2nd floor/elevator, balcony view looks over the neighboring county beach access and down the shoreline PERFECT for those summer fun & sunsets! Morning /Afternoon Walk on the 2 miles Santa Rosa Blvd.

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.

Penthouse-Huge Roof Top Patio w/ Hot Tub-LazyRiver
Our spacious Penthouse has amazing views on top of the world! Come enjoy our lovely condo with a roof top patio & private hot tub to see all of Okaloosa Island beach & bay for miles. Or have a romantic evening on the roof top patio with a huge hot tub that overlooks beautiful Choctawhatchee Bay. Located on Okaloosa Island at Destin West Beach and Bay Resort, this island connects Destin to Fort Walton Beach. We are on the bayside. We now offer 1 FREE set-up of beach service March 1-Oct.31st.

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.

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.

Islander Resort Okaloosa IsIand Beach Condo
Escape to Okaloosa Island and stay at this cozy studio condominium at the Islander Resort. This 6th-floor unit is perfect for couples or small families looking for a beach getaway. Wake up to stunning views of the Gulf of Mexico from the private balcony, relax on the pristine white sand beach, or take a dip in the Gulf-front pool. Take advantage of the resort's amenities, including a fitness center, shuffleboard, and barbecue grills.

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
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

Aloha Pool House- Stay Local, Live Aloha

Oceanview | Pool | Private Beach | Golf Cart

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

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

Clean & Luxurious Beachfront ~ 7 Pools+HotTubs+Gym

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

"SeaGlass" - Oceanfront with expansive balcony.

DestinWest Pelican Bayside, Lazy River, Hot Tub.

Beach front Condo with Beach service!

Incredible Direct Ocean View|2 Pools|Beach Chairs

GULF FRONT TopFloor Amazing VIEW Directly On Beach

Emerald Waters & Sugar White Sand!
Other vacation rentals with a pool

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

DW Sandpiper PH-08 ~ Lazy River ~ Penthouse!

Soundside Waterfront Condo

Surf Dweller 405 - Emerald Beach Hide Away

Yacht Club Living - Across the Street From Beach!

Okaloosa Oasis, Condo On the BEACH! Veteran owned!

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

Vitamin Sea
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$33,877 GYD | G$38,268 GYD | G$46,842 GYD | G$47,051 GYD | G$48,097 GYD | G$59,598 GYD | G$63,781 GYD | G$44,960 GYD | G$39,732 GYD | G$38,477 GYD | G$34,504 GYD | G$33,668 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 |
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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
- Seacrest Beach
- Henderson Beach State Park
- Navarre Beach Fishing Pier
- Village of Baytowne Wharf
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Aqua Resort
- Grayton Beach State Park
- Gulf Breeze Zoo
- HarborWalk Village
- Topsail Hill Preserve State Park
- Pier Park
- Fort Walton Beach Landing
- The Boardwalk on Okaloosa Island
- Jade East Towers
- Shipwreck Island Waterpark
- Pensacola Bay Center
- Camp Helen State Park
- Gulfarium Marine Adventure Park





