
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 2,700 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
Over 57,850 verified reviews to help you choose

Family-friendly vacation rentals
1,990 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
1,580 properties have a dedicated workspace

Wi-Fi availability
2,690 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.

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA
Islander Beach Resort is a 7-story structure of 114 condos on a short 2 mile stretch of Okaloosa Island and sits DIRECTLY on the BEACH. The building is painted aqua blue and gray, and all units overlook the ocean. There are 2 elevators and lots of parking. Guests can freely access the beach, HEATED pool, BBQ pits and parking area (a parking pass is needed from lobby). You will probably spend a lot of your time on our large private balcony overlooking the pool and beach, listening to the waves.

Beach Penthouse on Okaloosa Island in FWB, FL
Unit 301 has the best views being it is an end unit on the top floor. It also feels very spacious with its vaulted ceilings and unique loft area. Sleeps up to 6 people. Queen bed in Master. Another Queen bed and bath in loft. One full size sleeper sofa in living room. Owners have used the unit for past 9 years and have just decided to offer it as a rental. Freshly painted, and updated with new carpets, floors, furniture and appliances. Unit has everything you need for a wonderful vacation.

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.

Beach FRONT Condo-Pools-Lazy River-Free Beach Serv
Hello vacationers! You've found the perfect vacation spot! If you are searching for a beautiful, well-furnished condo with gorgeous 180 degree views of sugar white sand and emerald waters, then you have found the right place. This direct beachfront condo is on Okaloosa Island connecting Destin to Ft. Walton. It's a corner condo with sweeping, unobstructed views. Destin West Resort is in walking distance to so many attractions. FREE beach service included til Oct 31! Must be 25 or older to stay.

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.

Sunshine and beach time /Okaloosa Island
Snowbirds message me for winter rates! Steps to the sand, Ocean view , top floor unit, sleeps 6,(queen bed, single day bed, twin trundle,and queen sofa sleeper). USB port outlets, no carpet, stainless appliances, and keyless entry. A one minute walk to the white sand, wifi in the unit, 2 beach chairs, cooler, beach towels, and beach umbrella. Laundry onsite, Tom Thumb next door for items you might need. Everything for a great beach vacation!

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!

Direct Gulf Views, Private Pool, Sleeps 4
Wake up to the sound of waves and step onto your private balcony to watch the sun rise and set over the Gulf of Mexico. This beautifully appointed 1-bedroom condo sleeps 4 in a charming 9-unit boutique building — meaning no crowded elevators, no packed pool, and your own quiet slice of the Emerald Coast. Looking for a warm winter escape? Monthly rates and snowbird discounts available November through March.

Beachfront Bliss! Gulf Waves at The Palms #201
Wake up to gorgeous Gulf views at The Palms #201! 🌊 This beachfront 2BR/2BA end unit sleeps 6 with 2 king beds and a sofa sleeper. Enjoy water views from the living room, kitchen, and primary bedroom—then take the elevator down and step onto the sand. You’ll also get a reserved garage parking space and free daily beach service from March through October, including 2 chairs and an umbrella—a $40/day value! ☀️

Keeler Island Princess #508 Okaloosa Island Bchfrt
Escape the average life at the Majestic Island Princess. Reserve your time today at the Keeler Island Princess #508. Every angle in the living area provides a view so irresistible, you won't be able to take your eyes away from the enticing waters. The diamond sand sparkles with the sun's continuous movement in the sky. Each day, you will discover a new focal point and anticipate its return.

Okaloosa Island Top Floor 2BR Beach Condo
Welcome to the Islander unit 707, a cozy beachfront condo located on the seventh (top) floor of the Islander Beach Resort on Okaloosa Island. This charming two-beds, two-bathroom unit has everything you need for a comfortable and relaxing stay. Enjoy stunning views of the Gulf of Mexico from the private balcony or take a short stroll to the white sandy beach just steps away.

2nd floor beachfront with amazing views
Quiet, clean, and recently redecorated, this 2BR condo is right on Fort Walton's unique soft, white, sugar sand. Located in a quiet section of the much-desired Island Echos, this is the perfect place for your relaxing and fun beach vacation! You just can't beat this one for your getaway - we loved it so much we bought it! Guarantee you will love it too!
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Salt Pool & Spa, Heat Opt, Cali King Bed, Beach 4M

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

Sugar Sand Cottage at Destin Pointe

Touch of Madagascar-Whole House

Harbor Central Penthouse

Jade East 1250 Corner Condo, Spectacular View~Deal

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

Destin Miramar Walk To Beach Pet Friendly
Condo rentals with a pool

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach

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

DestinWest G405 Kid-friendly/oceanview/Lazyriver

Sola Azul | Gulf-Front Luxe + Beach Service

Beachfront Bliss 2BR/2BA Condo Stunning Ocean View

Destin West V409 Cozy Beach Getaway 7Amazing Pools

Ocean Views at Waterscape Resort!

Waterscape 5th Flr -Closest 1 Bedroom to the beach
Other vacation rentals with a pool

Waterfront end unit: VIEW! pool, pier, and beaches

Ocean view condo, Lazy River & Beach, Destin West

Beach front Condo with Beach service!

Gulf-Front Escape on Okaloosa Island (Veranda 203)

Sunset Dreamin! Gorgeous 2BR Panoramic Water Views

Newly Remodeled Beachfront w/ Amazing View Destin

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

Pool Table, Lazy River, & HUGE Patio! Destin West!
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 | ﺩ.ﺇ 595 | ﺩ.ﺇ 672 | ﺩ.ﺇ 823 | ﺩ.ﺇ 830 | ﺩ.ﺇ 992 | ﺩ.ﺇ 1,396 | ﺩ.ﺇ 1,120 | ﺩ.ﺇ 790 | ﺩ.ﺇ 698 | ﺩ.ﺇ 676 | ﺩ.ﺇ 606 | ﺩ.ﺇ 591 |
| 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
- Pier Park
- Henderson Beach State Park
- Village of Baytowne Wharf
- Frank Brown Park
- Seacrest Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Aqua Resort
- HarborWalk Village
- Grayton Beach State Park
- Gulf Breeze Zoo
- Topsail Hill Preserve State Park
- Fort Walton Beach Landing
- Jade East Towers
- Morrison Springs
- Shipwreck Island Waterpark
- Camp Helen State Park
- Gulf World Marine Park
- Pensacola Bay Center
- Johnson Beach





