Vacation rentals with a pool in Santa Rosa Island

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.

Top guest favorite

Guest favorite

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.

Top guest favorite

Guest favorite

Oceanfront 3 King BR/3BA Condo Steps 2 Sand & Surf

Experience the Gulf in a Newly Remodeled Condo! This family-friendly ground-floor unit offers ultimate convenience. The master bedroom has ocean views, a king bed with a pullout trundle. The second bedroom has a king bed with a trundle, and the third has a King bed. The living room includes a queen sofa bed. Each bedroom has a private bath and TV. Enjoy free beach service March–Oct with two chairs & an umbrella. Step onto the sand, relax, and unwind! Guests 27+ only. No smoking. No parties

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

Newly renovated! - Welcome to The Oasis, a luxury beach studio at El Matador Condos on Okaloosa Island, Fort Walton Beach, FL. Be our guest at this beautifully decorated, clean, comfortable studio, ideal for small families, small groups, couples, singles, & business travelers. You'll have direct access to the private beach & all the amenities including a seasonally heated outdoor pool, Gulf view pool, hot tub, sauna, gym, tennis/pickleball & basketball court, BBQ areas, & a laundry room.

DestinWest G405 Kid-friendly/oceanview/Lazyriver

[new patio furniture] Destin West Resort Gulfside 405 (2mins to the beach and pool) ~ 1 Bdr + 1 bunkroom with 2 full baths, Sleeps 6 ~ great ocean view ~ free beach service: 2 chairs & 1 umbrella (seasonal: 3/1 - 10/31, 9am-5pm) ~ 1 King Bdr with a private bathroom ~ 1 bunk room (2 twin beds, each with its own TV) with a private bathroom ~ 1 Q pullout sleeper ~ pack n play ~ 4 smart TVs ~ full kitchen stocked with cookware (Keurig and a traditional coffee maker). ~ washer/dryer

Destin West V409 Cozy Beach Getaway 7Amazing Pools

Newly updated modern beach-side unit. Luxurious renovated bathroom. This Gulfside unit is steps away from the white sandy beach, 7 different pools, and many restaurants. Located on the 4th-floor with one of the best views in the Florida panhandle. A 180-degree view of the emerald waters of the Gulf of Mexico, Choctawhatchee Bay, the Okaloosa Island sand dunes, and the Destin city-scape. Relax in the lazy river pool, sunbathe at the beach, or spend your day being adventurous.

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!

Top guest favorite

Guest favorite

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.

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!

Top guest favorite

Guest favorite

Gorgeous Gulf Front condo with amazing views!

Your romantic Gulf-front getaway begins here and is a top-rated destination for couples...This recently updated condo offers new furnishings and is tastefully decorated in warm blue-grey and emerald tones - perfect for a seaside vacation. The Gulf views from your private top floor balcony are unparalleled and promise amazing sunsets.