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Gulfport Rentals with Pools

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1,880 house rentals in Gulfport with pools

Gulfport Waterfront Mid-Century Modern Masterpiece

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$333

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$149

"Lovers Den" Your Hidden Private Gem

Gulfport condo

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$91

Resort Style Living

Gulfport house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 34 minutes

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Price per night from

$418

NEW! Cozy Beach Apt. w/ Pool, 3 Mi to St. Pete!

Gulfport apartment

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 5 minutes

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Price per night from

$113

SunKissed....(heated) POOL HOME!

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$385

3 bedroom, 2 bath home with a pool and Florida room, near Gulfport Waterfront

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 58 minutes

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$246

NEW! Cozy Cottage Retreat: 2 Mi to Gulfport Beach!

Gulfport cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 5 minutes

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$101

NEW! Cottage w/ Fire Pit ~ 3 Mi to St Pete Beach!

Gulfport cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 5 minutes

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Price per night from

$101

Great rentals within 20 miles that match your search

Beachfront 7th Floor Studio. Breathtaking View.

North Redington Beach apartment

/ 1 bathroom / sleeps 2

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Price per night from

$77

Cove Cay Condo

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$54

Lovely Pool Home close to the Beaches

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$161

beautiful condo with magnificent views of mandalay

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$114

Beautiful Updated Beachfront 2BR/2BA Condo

Madeira Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$130

Wonderful Belleair Beach Condo

Belleair Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$98

Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

“Great Value Stay in Paradise aMI!” This is a lovely spacious condo, nicely furnished, with decent wifi, aircon and all mod cons. The condos in the Sandy Point complex all share a pool and we found this to be very clean, nicely warm and never too crowded. Although it's on the quieter side of the island we liked the location - it's a five minute walk from Publix, even less to the free Island Trolley Bus, and less than 10 minutes to the beach for those amazing sunsets :-) The equipment cupboard allowing us to borrow beach chairs, swimming noodles, buckets and spades etc was much appreciated. Having looked around at other rentals we found this condo to be very keenly priced. Andrew and Jo were very pleasant and easy to deal with and we will definitely stay again some day.

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$133

Oceanfront 1400 sq ft Condo at Beach Cottage One! Private Beach, Big Pool

Indian Shores apartment

2 bedrooms / 2 bathrooms / sleeps 4

“We had a great vacation at this condo.” My family has been visiting indian rocks beach for nearly two decades, and we continue coming back to this resort and specifically, Martin's condo. It is always kept updated and we had a nice relaxing stay. It has WiFi for the kids and has a picture perfect view of the beach, ocean, sunsets and pool deck. You won't be disappointed.

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$212

MERMAID 2BR beachfront home***Heated Pool***Pets OK

Indian Shores house

2 bedrooms / 1 bathroom / sleeps 6

“Clean and Comfy Classic Beach Cottage steps away from the gulf sands.” Ideal quiet location on the shore and within walking distance of restaurants. Cottage was nicely decorated with warm wood paneled walls and tile floors. Bed was comfortable and bath spotless. Liz was a great host and the daily sunsets outside our window were awesome.

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$228

Seashell #15 Quiet & Relaxing Condo

Indian Shores apartment

2 bedrooms / 3 bathrooms / sleeps 4

“Loved it!!!!!” The location is convenient to the beach, great restaurants and shopping. The condo is more like a home, immaculately kept and well equipped with everything from a cart to haul your beach chairs to a blender to mix your Margaritas! I would have stayed here again next year if it wasn't already booked.

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$139

Coquina Sands, view beach from balcony, priv pool

Holmes Beach house

2 bedrooms / 3 bathrooms / sleeps 6

“Great place, great location, great vacation” We stay at Anna Maria for 12 days and if we could we would be there for 12 years. Awesome place and great host. Everything was ready for us. Only high marks. Thanks

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Price per night from

$245

2 bedroom condo, Coquina Key, Tampa Bay, Florida

St. Petersburg apartment

2 bedrooms / 1 bathroom / sleeps 4

“Waterside at Coquina Key has it all!” Waterside at Coquina Key is a a well kept up gated community that offers all the amenities a wonderful vacation requires. Marlean's condo provides a nicely updated unit that allows you to enjoy the waterside condos in comfort and provides all the extra's you need to relax and unwind in the peace and tranquility of a watersdie property. The kitchen had all you needed and more and was nicely updated and contained all you need to cook in or prepare a quick breakfast and take off for the pool or to work-out. The only small downside is not to have a wash and dryer available in the unit. Although one is available 24/7 as the clubhouse and you can use your debit card to work them. the beds were comfortable, and the living area had ample seating available. Thank your for shring your condo, it was wonderful.

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$85

Penthouse with enchanting ocean views - No Booking Fees. Contact Owner.

Indian Rocks Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect” We stayed here last year(this years holiday reminded me I really need to leave some feedback). My family absolutely loved this Condo, location was perfect, you really do just look onto the Gulf. The only thing between you and the beach is the pool, which makes it even better. Leaving the beach there was nothing better than a quick cool off in the pool before heading up to the condo( via the lift which takes you directly to your own private balcony). On lazy days parents were able to sit on the balcony and let the kids leave the condo via the lift and watch them go down to the beach and play, no roads or other distractions. Previous comments didn't like the couch- it's leather and green no big deal, personal tastes. There were a couple of loose tiles on the bathroom floor but again no big deal, the spa bath more than made up for it. If I was staying at Indian rocks again( which I might because the area is great) then this condo would be first on my list.

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$157

Mintfish, beautiful views across Bimini Bay! 4-Bed

Anna Maria Island villa

4 bedrooms / 4 bathrooms / sleeps 8

“Great View!” The best thing about this home is it's location on Bimini Bay. Beautiful pool and view out over the bay. The home is decorated in a happy motif, although the beds were deemed hard as boxes by a couple of our guests. Kitchen is sufficient for cooking basics, and has nice appliances. Overall a nice stay on a quiet, north end spot of the island.

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Price per night from

$415

Clearwater Beach 3-bedroom Waterfront Luxury Condo

Clearwater condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 35 minutes

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Price per night from

$229

Oceanfront Condo at Beach Cottage One. 1400 SQ Ft with 2 King Beds.

Indian Shores apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$212

HOME AWAY FROM HOME ..

Indian Rocks Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay in Indian Rocks Beach” My wife and I celebrated our 31st anniversary and stayed in Sharif and Sabine's condo 202 Reef Club 1000 Gulf BLVD. They bent over backwards to make sure our stay was incredible. They asked us to do a quick run through of the unit and if there was anything dirty or needed repair to call immediately. We called on a toilet issue and over the phone we repaired it within minutes. They also had beach chairs umbrella and toys to play with so we did not need to bring anything with us. We are looking forward to our next stay. I have business in Tampa and usually stay at a hotel. if this unit is open, it was less expensive and had tons more room.

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$1,146

Luxury waterfront corner townhome on Tampa Bay :

Ruskin hotel apartment

3 bedrooms / 3 bathrooms / sleeps 8

“Immaculate and Peaceful retreat with great amenities” We had a wonderful stay in this beautiful townhouse in Ruskin, FL. We spent the Thanksgiving holiday there with our 2 toddlers, and visited with grandparents nearby. The home is beautifully and tastefully furnished, absolutely comfortable and inviting, and with a true chef's kitchen stocked with all the cooking and eating utensils/applianced we would have at home. The bedrooms are on the top floor: the master bedroom has a gorgeous ocean view and the balconies are large enough for table and chairs to sit and have coffee/eat outside. The kitchen area is open to a great eating area as well as visibility to both the smaller living area in the kitchen/dining suite as well as great visibility into the large livingroom (anyone with kids will note how important this is for toddlers!). The townhouse comes with full washer/dryer, as well as all the white linens / towels one would need. It was immaculate, clean, and just enjoyable to stay there. It feels brand new, and has been well taken care of by the owner and guests. The home is a very short walk down to a private white sand beach where beach chairs and umbrellas are available. One also has access to a great spa/pool. There is a restaurant on the premisis of the resort that is fun and inviting. All in all, we were warmly welcomed and have a lovely stay. We will certainly be coming back and highly recommend this home away from home to anyone looking for a nice break.

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Price per night from

$172

Limefish, spectacular beachfront location!

Anna Maria Island house

3 bedrooms / 3 bathrooms / sleeps 8

“Grand getaway for Yaya and her kids and grandbabies!” We stayed a week at the beginning of September and loved everything about the place. Megan at Sato Realty is the best! once you have groceries in, you never have to leave, or get back in the car! Everything a beachfront paradise should have. My psychiatrist recommends aMI every 3 months!!!

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Price per night from

$587

Plumfish, located on the Hammock Bayou. Beautiful!

Anna Maria Island house

3 bedrooms / 2 bathrooms / sleeps 8

“Plumfish is a great place to relax and enjoy anna Maria Island” Four phrases that would describe Plumfish are "very private and quiet" "extremely clean" "spacious and well decorated" and "convenient location" We enjoyed the heated pool and scenic dock. We were impressed with the great kitchen and bathrooms. We liked Plumfish so much we've already made arrangements to return next year.

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Price per night from

$225

Honeyfish, stunning views across Bimimi Bay!

Anna Maria Island villa

4 bedrooms / 4 bathrooms / sleeps 8

“Best rental on AMI” This is a classy place to stay. Situated toward the north end of the island at the extreme end of the cul-de-sac that is Tarpon Street, this property could not be better sited as a base to explore and enjoy Anna Maria Isand. Within a 4-5 minute bike ride are gulf side beaches, the Sandbar beach restaurant (have dinner watching the sun go down at a table with your toes in the sand while having great food), City Pier, Ginny & Jane's for breakfast, Beach Bums for all rentals needs (kayaks, paddleboards, Bikes etc.), the general store for food (check out their cuban sandwiches), beers and wines, as well as a host of boutique shops. The Rod n Reel Pier (my favourite) is a little further but has a great little bar and a restaurant that you have to try out. Draft Budweiser is $1.50 and comes in a plastic cup so you can take it outside to watch the fish swim under the pier and the pelicans dive for food. Honeyfish is a canal facing property at the end of Tarpon Street so no through traffic by car, bike or on foot. Very private. Not only is it canal facing - it has what has to be the best canal view possible with far reaching views over Bimini Bay rather than simply looking at another house over a canalway. The house is large, with 4 bedrooms and 4 bathrooms. Furnishings and fittings are of a very high standard and enhance the luxury feel of the place. Equipment such as televisions, sound systems, kitchen aids and washing facilities are all excellent. On arrival, the great room comprising kitchen, dining and living rooms seemed much larger than the photographs on the rental company website. Outside there is a large canal facing deck with ample seating. To the side is a large swimming pool which is screened in from view from the canal for privacy. If it gets a little hot at the beach, then head back to the house and jump in the pool to cool off for a while. From the dock or even from the sofas in the living room, watch the wildlife over Bimini Bay. Exotic birdlife, jumping fish and dolphins were all frequent visitors. This is a gem of a place. A truly relaxing environment in a quality setting. It may not be a cheap place to stay but I would recommend pushing the boat out. Having THAT view in THAT location made all the difference to our holiday. There are cheaper places to stay for sure but there is only one Honeyfish. You will not be disappointed. I would return in a heartbeat and would recommend it to anyone as an ideal vacation base on a wonderful holiday island.

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Price per night from

$415

Beach Dreams - Beach Cottage 2103

Indian Shores apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great unit, perfect location” Been coming to Beach Cottage for over ten years and love the decor and location of Beach Cottage 2103. Indian Shores Vacation is the only place we think of for summer beach vacation.

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Price per night from

$229

Clearwater, Florida 2 Bedroom Fully Equipped Condo

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Location” Excellent location, close to beach and shopping, very clean unit. Loved that there were beach chairs and lots of towels available. Owners were easy to deal with and very cooperative. I would definitely rent this condo again.

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Price per night from

$73

Avalon at Clearwater

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

“Location,Location,Location” Terrific get-a-way. Quiet, comfortable ,very clean, has everything you could want .Very close to other locations such as Tampa ,Dunedin. Beautiful beaches. Fabulous sunsets. .Great restaurants within walking distances. Condo has a beautiful pool. Truly a paradise . A must rental.

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Price per night from

$115

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$101

Enjoy a Florida Vacation in a beachfront condo!

Madeira Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$201

Spectacular Beachfront Condo-Private Beach/No Fees

St. Pete Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$225

**PERFECT FOR A FAMILY VACATION** 3Br Directly On The Beach

Indian Shores condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 22 minutes

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Price per night from

$179

Beautifully updated Clearwater Condo- 20-25 Minutes to the Beach

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$189

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