
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.

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.

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

Amazing Top-Floor Condo, Free Beach Service!
Decorated in soothing designer colors with a coastal feel, the unit has 2 bedrooms with comfortable king size beds, flat screen TVs and private bathrooms; two bunk beds in a hallway alcove; 2.5 bathroom, and open concept full size kitchen with all new full size stainless steel appliances, dining area and living room with a sleeper sofa. The unit sleeps eight. Plus, you'll have access to all of Waterscape Resort's fabulous amenities! Complimentary beach service with 2 beach chairs and umbrella.

Newly Remodeled Luxury Studio-Beach/Pool/Hot Tub
Welcome to Surfboards Island Condo! This property is located on the beach. It is a studio located on the ground floor of building 6 next to the tennis courts. Decorated in a coastal surf motif, the unit is well equipped and cozy. The kitchen is fully furnished with everything you need to make a great meal. There is a king size bed and a sofa sleeper that will accommodate 4 people in the unit. The extra large TV is viewable from anywhere in the condo. This unit is next to the seasonally heated

Cheery Condo-Free Beach Service-Direct Ocean View!
Let your cares literally drift away in this relaxing, kid-friendly, beautifully decorated condo with a King bed w/bath + twin/twin bunk area w/bath - Queen LR sleeper sofa. Enjoy stunning views of the Gulf of Mexico and pool area from your private balcony. We invite you to enjoy your special vacation at this perfect Emerald Coast paradise. Free beach service (2 chairs and umbrella) is INCLUDED! (March 1-Oct 31). *Note - Okaloosa County Tourist Tax of 6% will be applied to this booking.

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.

Ocean view condo, Lazy River & Beach, Destin West
From your unit on the Gulf side of the resort, enjoy the spectacular ocean view, award winning lazy river, and many pools in this family friendly Destin West Beach and Bay Resort with private beach. Your unit is a couple blocks from Gulfarium Marine Adventure park, where you can swimming with dolphins. Enjoy the Broadwalk Okaloosa Island with seaside shops, eats, and entertainment within a block. Okaloosa Island fishing pier is within 2 blocks for fishing enthusiasts.

Ocean Views at Waterscape Resort!
Experience everything the stunning Emerald Coast has to offer while staying in our beautifully updated condo, with expansive ocean views including everything you need for a comfortable stay! Enjoy the Waterscapes resort amenities including direct beachfront access, beach chairs & umbrella, lazy river, zero entry pool, kids water play area, a separate heated pool for the cooler months, hot tubs, propane grills, a full gym, on site tiki bar, and free gated parking.

Waterfront Paradise•2.5 Miles from Beach•Boat Slip
🌴 Beautiful studio condo, centrally located in Ft. Walton Beach! Waterfront on the Santa Rosa Sound 🌊, adjacent to the Gulf, with views overlooking a large, inviting pool 🏖️. Walking distance to restaurants 🍽️, and just 10–15 minutes to Okaloosa Island & Destin beaches, attractions, and shopping 🛍️. Navarre is only 20 minutes away! Located on the 2nd floor with elevator access 🛗, plus a private marina ⚓. Starter pack of supplies included 🧻✨

Veranda 102 - Direct Beachfront - Gulf Side Pool
Small quaint 9 unit complex. Direct BEACHFRONT on the white sand of Okaloosa Island, FL. Completely remodeled! Breathtaking views of the emerald green waters of the Gulf of Mexico (and dolphins) right from the private patio! Gulf side pool (not heated). Contactless check-in. Walk 1 mile to the Pier & Boardwalk and restaurants. 15 minutes to Ft. Walton Airport. 2 person beach service (1 umbrella & 2 chairs) available 3/1 - 10/31

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!
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Emerald Coast Escape

* NEW * 3BR Pool & Hot Tub l 10 min to Beach

Sugar Sand Cottage at Destin Pointe

Its 5 o'clock here

Bay and Beach Relaxation

Aloha Pool House- Stay Local, Live Aloha

#2 4BR HUGE PET Friendly Home Away from Snow!

Destin Beach House• Sleep24•Hot Tub•Pool •RoofDeck
Condo rentals with a pool

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

Destin West Villa PH01 ~ Penthouse w/ Hot Tub

Okaloosa Island Beach Condo5/Small Pet/Pool/Grill

"SeaGlass" - Oceanfront with expansive balcony.

Beach front Condo with Beach service!

GULF FRONT TopFloor Amazing VIEW Directly On Beach

Direct Beach FRONT-Amazing Views-Lazy River-Pools!

Condo With Serene Panoramic Views of the Gulf
Other vacation rentals with a pool

Wonder 2403 Miramar Sand & Sip

Stunning IBR 403 Gulf Front w/ Beach Service for 2

Beachfront! Newly remodeled! Corner Unit!

Remodeled 2025! Beachfront Destin West -Lazy River

Your Little Slice of Paradise

Luxury Pool/SPA/BEACH, 1BR w/Dol Views, Full KITCN

2 Bedroom Condo on the Beach at Okaloosa Island

Spectacular 3BD- 3.5 BA at Redfish Lake
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$33,904 GYD | G$38,299 GYD | G$46,880 GYD | G$47,089 GYD | G$48,135 GYD | G$59,646 GYD | G$63,831 GYD | G$44,996 GYD | G$39,764 GYD | G$38,508 GYD | G$34,532 GYD | G$33,695 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$14,650 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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- 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





