Gulfport Getaway
- Address: 5429 Essex Ave S.
- Location: Gulfport
- Type: House
* Only 400ft to Public Beach Access
* 4BR Family Home with Awesome Bay Views
* Two Large, Private Balconies
* Great Space for Larger Family or Couples
* Walkable to Restaurants, Shopping, and a Park
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing.
Immerse yourself in the laid-back, beach lifestyle in this 4 bedroom, 3 bathroom home in Gulfport. This beautiful home is as amazing inside as the surrounding area it sits in! Gulfport is a quaint, low-key town that has a number of great restaurants to choose from and loads of local shops for you to enjoy during your stay. All within walking distance from this awesome home!!
There are 3 levels to this home; ground level will be parking, the middle level is your living/dining area with a bedroom and full bath. There are 3 more bedrooms upstairs as well. The kitchen is fully stocked and equipped with all the essentials you need for creating delicious meals and memorable moments. The main level bedroom is set up with a Twin Trundle bed, giving you 2 twin beds for sleeping options on that level. The upper level has 2 bedrooms that are equipped with a King bed in each, the 3rd upper-level bedroom has a Queen bed so that all guests have a quiet, comfortable space to retreat to after a full day in the sun! Another awesome perk to this house is that you have not 1, but 2 private balconies to relax on, savor the coastal breeze and breathtaking water views and just unwind as you soak in the surroundings.
The Bed Set Up:
Main Level: Twin with Twin Trundle Pullout Bed
Upper level bedroom 1: King Bed
Upper level bedroom 2: King Bed
Upper level bedroom 3: Queen Bed
*Please Note: Stairs are needed for access to this home
Gulfport gives off a "Key West Style" Florida vibe with its brilliantly colored homes and businesses, locally owned and operated shops and hints of local art all over the town! Right down the road you will find the Boca Ciega Bay and Gulfport Beach access, with the Gulf of Mexico beaches only a few miles away to your west. The heart of Gulfport has fantastic dining options! Try Stella’s for breakfast, O'Maddy's for lunch, Pia’s Trattoria for dinner; the list goes on and on. Live music, shops and ice cream parlor, art galleries, marinas, and great attractions are all right here! Spend time in the many parks nearby, including Chase Park that has tennis and pickleball courts, and don't miss the Tuesday Farmers Market and Artwalk! If this will be your first visit to Gulfport, we promise it will not be your last!!
Twin with Twin Trundle
- Adventure
- Air Conditioning
- Balcony
- Beach
- Beach Combing
- Bed Linens
- Bird Watching
- Boating
- Coffee Maker
- Cycling
- DeepSea Fishing
- Dining table
- Dishes & Silverware
- Dishwasher
- Dryer
- Family
- Fishing
- Fishing - Bay
- Fishing - Surf
- Free Parking
- Free wifi
- Hangers
- Heating
- Hospital
- Hot Water
- House
- Iron & Ironing Board
- Jet Skiing
- Kitchen Island
- Laptop Friendly
- Living Room
- Long Term Stays Allowed
- Microwave
- Near Ocean
- Outdoor
- Outlet Shopping
- Oven
- Para-sailing
- Parking
- Private Entrance
- Refrigerator
- Restaurants
- Romantic
- Shelling
- Shopping
- Smoke Detector
- Sports Activities
- Stove
- Street Parking
- Swimming
- Television
- Toaster
- Towels
- Walking
- Washer
- Water View
- Watersports
- Wifi
- Wildlife Viewing
- Wireless Internet
Plan ahead for sunshine and savings in St. Pete Beach. Book your Summer 2027 getaway between May 22 and August 7 and enjoy up to 12% off stays of 7+ nights. Use code GETAWAY2027 and lock in your perfect beach escape from now through August 16, 2026.
*Offer valid on new online bookings made by August 16, 2026, for stays of 7+ nights for travel between May 22, 2027 and August 7, 2027. Offer cannot be combined with other promotions or discounts, and exclusions and restrictions may apply to select properties.
Enjoy 10% off your summer escape when you stay between June 2 and September 1, 2026. Book 3 nights or more and make the most of peak season for less.
Use code HOTDEALS at checkout.
*New online bookings only. Minimum stay required. Restrictions apply.
Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.
*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.
This house was great! Frankly, it was the most 'homey' VRBO that I've rented in a long, long time. It felt so much like a fun beach house! The house was perfect, communicating with the host was easy, the kitchen held everything needed for cooking meals, there were beach chairs and towels for taking to the waterfront, it was all great. The only negative aspect was that on Fri and Sat nights, the bars directly across the street were playing loud music which could be heard in the master bedroom upstairs, but as long as you're not going to sleep early, it's really fun to sit on one of the great balconies and enjoy their music! Candidly, this is one of the few properties that I would absolutely rent again if the opportunity were to arise. I would recommend this place to my friends and family.- Reviewed On: 7/22/2026
- Check Out On: 7/20/2026
Thank you so much for your wonderful review! We're thrilled to hear that our home felt welcoming and gave you that classic beach house experience. It means a lot to know it was one of the most comfortable and enjoyable vacation rentals you've stayed in. We're glad you found the home well-equipped, enjoyed the beach chairs and towels, and that communication with us was easy. It's especially rewarding to hear that you would rent with us again and recommend the property to your friends and family—that's the highest compliment we could receive. Thank you as well for mentioning the weekend music from the nearby bars. While the lively atmosphere is something many guests enjoy, we understand it may not be ideal for those turning in early, and we appreciate you sharing that perspective for future guests. We truly appreciate you choosing to stay with us and look forward to welcoming you back for another beach getaway!Resort Rentals staff
Wonderful place. Great location and very clean!- Reviewed On: 5/25/2026
- Check Out On: 5/25/2026
Thank you, Liliana. Glad you found the place wonderful, the location great, and the unit very clean. It was a pleasure hosting you, and we’d love to welcome you back.Resort Rentals staff
Cute house, great views and convenient location.- Reviewed On: 4/24/2026
- Check Out On: 4/12/2026
Thank you for your lovely review! We're so glad you enjoyed the house, the beautiful views, and the convenient location. We hope to host you again for another great stay!Resort Rentals staff
House very clean and lots of room. Very close to downtown and beach. Excellent stay- Reviewed On: 2/23/2026
- Check Out On: 2/23/2026
Great house with tons of space and comfy beds. Very spacious and easy access. I would absolutely stay here again.- Reviewed On: 1/19/2026
- Check Out On: 1/19/2026
Thank you, Samantha. Glad you enjoyed the spacious house, comfy beds, and easy access. Happy to hear you’d stay here again. It was a pleasure hosting you, and we’d love to welcome you back.Resort Rentals staff
The property exceeded our expectations. The Management was wonderful and rapid response which was appreciated. Blankets could have been better quality. The use of the garage was a special offer, but would be wonderful for al guests to have.- Reviewed On: 1/5/2026
- Check Out On: 1/3/2026
The house has a great set up. It was clean and the location cannot be beat. I wish the palms didn’t block the view but understand the evening sun might be intense. Perfect place for our family Christmas.- Reviewed On: 12/30/2025
- Check Out On: 12/15/2025
Great house, near lots in Gulfport- Reviewed On: 12/2/2025
- Check Out On: 11/30/2025
Thank you! We’re glad you enjoyed the house and the convenient Gulfport location. We’d love to host you again anytime!Resort Rentals staff
This place was an amazing location and good for the price. We will try to stay here again in the future.- Reviewed On: 11/2/2025
- Check Out On: 11/2/2025
Thank you, Jake. We’re glad the location and value worked well for you. It was a pleasure hosting you, and we’d love to welcome you back.Resort Rentals staff
We had a great experience in this home, we had plenty of room and the home had everything we needed for our week long stay. The Gulfport neighborhood was great as well, we really enjoyed the neighborhood shops and restaurants. We will definitely stay again when visiting Florida.- Reviewed On: 6/2/2025
Thank you, Rudolpho, for the wonderful feedback! We're so glad to hear the home had everything you needed and that you had a great experience during your stay. Gulfport is a special place, and it's great to know you enjoyed the local shops and restaurants too. We'd be delighted to host you again on your next visit to Florida!Resort Rentals staff
This was the perfect place for my family to stay. We loved being able to walk to the local beach and restaurants. It was also close to other beaches in the area that we loved visiting!- Reviewed On: 4/21/2025
- Check Out On: 4/21/2025
Great location. Lots of space.- Reviewed On: 4/13/2025
- Check Out On: 4/13/2025
Great stay at Gulfport getaway! Gulfport was fun and nice to have places to eat and drink at right in town. The area was hit pretty bad by the hurricanes but the community was lovely! We loved O’Maddys and Pia’s especially.- Reviewed On: 3/29/2025
- Check Out On: 3/29/2025
Thank you for your review, Madeleine! We're glad to hear you had a great stay at Gulfport and enjoyed the local dining options. It's wonderful to know that you loved O’Maddys and Pia’s. We hope to have the pleasure of hosting you again soon!Resort Rentals staff
Great place and great location. Definitely book again.- Reviewed On: 3/23/2025
- Check Out On: 3/23/2025
Thank you for your review, Steve! We're pleased to hear you enjoyed the location and your stay. We look forward to welcoming you back for another visit!Resort Rentals staff
Great home and location!- Reviewed On: 3/14/2025
- Check Out On: 3/14/2025
Thank you, Joshua, for your kind feedback! We're glad you enjoyed the home and its location. We hope to host you again soon!Resort Rentals staff
We had a great stay! Everything we needed and very comfortable. The house was in a great location! We will be back for sure.- Reviewed On: 3/3/2025
- Check Out On: 3/3/2025
Thank you for your review, Adam! We're glad to hear you had a great stay and found the house comfortable and well-located. We look forward to welcoming you back for another visit!Resort Rentals staff
we rented the house as a base camp for a sailboat regatta in St. Petersburg and it worked out perfectly. Only 18 minutes trip to downtown whatever time of day. It was very clean, plenty of private bedrooms and bathrooms. Relaxing decks. One block walk to shops and restaurants and the charm of Gulfport. We are already planning the next trip.- Reviewed On: 2/17/2025
- Check Out On: 2/17/2025
Fantastic home in a great location!- Reviewed On: 2/8/2025
- Check Out On: 2/8/2025
Thank you for your review, Andrew! We're pleased to hear that you found the home fantastic and enjoyed the great location. We hope to have the pleasure of hosting you again in the future!Resort Rentals staff
Place was great, the elevator did not work so that was a bit of a bummer. Other than that it was perfect.- Reviewed On: 7/21/2024
- Check Out On: 7/21/2024
Thank you for reviewing! We hope you will return for future vacations!Resort Rentals staff
Awesome house and convenient to some neat bars and restaurants.- Reviewed On: 7/19/2024
- Check Out On: 7/19/2024
Wonderful Rob! glad you enjoyed your stay at Gulfport Getaway and found the house awesome and conveniently located to bars and restaurants. We hope you relaxed and will join us again for another stay!Resort Rentals staff
5 college friends and I rented the house for our annual reunion. The house was absolutely beautiful and clean. We had a small issue with getting the elevator (I'm disabled) to work and I immediately called the helpline and April answered the phone. She was so nice and very helpful. She contacted someone to help us. I was on hold for a short amount of time and she got back with me and talked me through the situation. I then hung up and we did everything she suggested and it worked! I then called April to let her know we found and fixed the problem. She was as happy as we were! The location of the house was perfect. We could walk to the pier, beach and restaurants. We really enjoyed sitting on the balcony at night listening to the bands who were performing at the bars across the street. I will definitely let people know about this house and Resort Rentals if they need to rent in the future.- Reviewed On: 7/1/2024
- Check Out On: 7/1/2024
Wonderful Sandra! how fun to have a annual girls reunion at Gulfport Getaway! Glad you and your college friends found the house absolutely beautiful with a great location, and clean. That is great April at Resort Rentals was quick to assist you with the elevator. Wonderful it is in walking distance to the pier, beach and restaurants as well as, sitting on the balcony you could listen to the musical performance from the bar across the street. We hope you all relaxed, enjoyed reconnecting. Thank you for recommending the property, and will join us again for a future stay.Resort Rentals staff
Very nice rental. Had a great time. Looking forward to my next trip.- Reviewed On: 6/16/2024
- Check Out On: 6/16/2024
Thanks Jeff! Can't wait to see you again!Resort Rentals staff
Very cute house. Walking distance to restaurants, coffee shop and a recreation center right across the street. Definitely would stay again.- Reviewed On: 5/27/2024
- Check Out On: 5/27/2024
Thank you for the great review, Gisselle! We're glad to hear you enjoyed the convenient location. We look forward to hosting you again in the future!Resort Rentals staff
Had a wonderful girls weekend away! Perfect location. Beyond adorable area with so much to explore within walking distance. House was fantastic!- Reviewed On: 3/11/2024
- Check Out On: 3/11/2024
Thank you Megan!! So glad you enjoyed you stay. We hope to see you again!Resort Rentals staff
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