
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.

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!!

Direct Beach FRONT-Amazing Views-Lazy River-Beach
☀️ Direct Gulf-Front Condo | Best Views & Resort Perks! 🌊 Stay in our 4th-floor corner condo at family-friendly Destin West Beach & Bay Resort, w/ unbeatable 180° Gulf views from a wrap-around balcony! 1 of only 10 true beachfront condos, you'll enjoy unobstructed ocean views plus a 700-ft Lazy River, a 5,000 sq. ft. pool, 2 seasonally heated pools, hot tubs, a zero entry pool, & more! Best of all, we offer 1 free beach service setup with our condo thru Oct. 31st. Must be 25 or older to stay.

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.

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.

Free Chair Service-Beachfront 4th Floor
Beautiful fourth-floor balcony views of beachfront, barrier island chain, and sound area! Exceptionally convenient white-sands beach access and gorgeous emerald waters! Enjoy indoor/outdoor pool and on-site gym. This beach condo is not only fantastically located on the quieter end of Okaloosa Island, but also comes with modern, coastal-themed furnishings. Access the Destin and Fort Walton Beach attractions only a few miles down the street. Includes free chairs and umbrella on the beach!

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.

Beachfront-Top Floor-West Corner-Free Bch Bch+ Gym
If you’re wanting a vacation where you can sit on your private balcony and enjoy colorful sunsets, sweeping views of the gulf, dolphins playing in emerald green water, seagulls floating by on warm tropical breezes, you need look no further! Welcome to the best of Destin West Gulf Front! This top floor, direct gulf-front condo corner condo offers the perfect vacation spot for that special vacation time. FREE BEACH SERVICE and FITNESS ROOM PROVIDED!

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

Emerald Waters & Sugar White Sand!
Enjoy all the comforts of a North American lifestyle with a modern contemporary look and stunning Gulf-front views from our high-floor corner unit. Located right on the beach with no roads to cross and close to Destin. High-speed Wi-Fi, keyless entry, smart TV, beach towels, starter amenities, a seasonally heated Gulf-front pool (March 1–April 30 & Oct 1–Dec 31, subject to change) and MORE. Have a sunny day!

Beachfront condo with views
Gulf Dunes 105 – Gulf‑Front & Beachfront Feel the island vibes in this updated 1‑bed, 1.5‑bath condo on Okaloosa Island! Sleeps 6 with king bed, hallway bunks, and sleeper sofa. Enjoy a private balcony with Gulf views, direct beach access, pool, and free beach service (Mar–Oct). Walk to the Boardwalk for food and fun. Perfect for couples and small families. Heated pool 84–85 degrees (Nov–Mar).
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Private POOL- Gated beach access-backyard

Sugar Sand Cottage at Destin Pointe

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

Pool - Block to Beach - Golf Cart - Beach Service

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Harbor Central Penthouse

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

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

Sandy Cheeks/Okaloosa Island

Destin West V402/Gulf Front/Beach Service included

Destin West V409 Cozy Beach Getaway 7Amazing Pools

Waterpark Condo with Free Beach Setup & Aqua Pass

BayviewPerch - 2BD Bay Views & Golf Cart Sandestin

GULF FRONT TopFloor Amazing VIEW Directly On Beach

Star Of The Sea

Colorful Paradise Okaloosa Island Umbrella, Chairs
Other vacation rentals with a pool

Unit #6 Waterfront + Heated Pool and Spa Access

Gulf Front #2002 ETW 3King /3Bath Renovated

Paradise at Dune Pointe - Penthouse | Ocean views|

Home on Bay-Private Pool-Boat Access-Kayaks-Fish!

Tropic Like It’s Hot! 2 minutes walk to the beach!

Gorgeous 2BR With Panoramic Water Views

Gulfside Gem V306 (Heated Pool & Hot tubs)

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$33,872 GYD | G$38,263 GYD | G$46,836 GYD | G$47,045 GYD | G$48,090 GYD | G$59,590 GYD | G$63,772 GYD | G$44,954 GYD | G$39,727 GYD | G$38,472 GYD | G$34,500 GYD | G$33,663 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$14,636 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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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Aqua Resort
- Seacrest Beach
- Opal Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Village of Baytowne Wharf
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- HarborWalk Village
- Fort Walton Beach Landing
- Henderson Beach State Park
- The Boardwalk on Okaloosa Island
- Shipwreck Island Waterpark
- Topsail Hill Preserve State Park
- Camp Helen State Park
- Gulfarium Marine Adventure Park
- Pier Park
- Gulf World Marine Park
- Jade East Towers





