Vacation Rentals & Apartments in Kailua

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9,279 apartments

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$251

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$213

Beautiful 6 Bedroom Home in Reunion Resort and Spa

Reunion house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 14 minutes

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$488

Disney Pool Home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$218

The Guadalupe Tree Haus at Joshua Creek Ranch

Boerne house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 18

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$2,636

Spacious Disney pool home w/ Spa, near golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“PERFECT FAMILY VILLA!” This villa is HUGE and gorgeous! We were traveling with a large family and with 7 bedrooms and 9 beds plus a crib in the master there is more than enough room for your whole family to enjoy a get away! There are 2 rooms located down stairs so if anyone is disabled they can use these rooms. This home is beautifully decorated and so comfortable for us. We thoroughly enjoyed the screened in private pool -with a bathroom entrance right off the pool area! We felt very safe in the community this villa is in and the area surrounding it. Champions Gate is a gorgeous little community with everything you need within 10 minutes. We were visiting Disney and found this villa a wonderful option to staying in the parks. It took us 15 minutes to get to any park and we always parked and loaded a tram quickly and went right to the door. I don't know why people have always convinced me staying of property would be such a hassle..it was no hassle at all! A lovely bonus to this villa was an ice cream truck driver lives right down the street and hits the neighborhood 2 times a day. The kids LOVED that! The home came with all the comforts needed to make us feel at home. Including pool toys, 2 high chairs, iron/ironing board, hair dryers, big beach towels, bath towels and rags, kitchen towels and all the cooking utensils and appliances needed for cooking meals. We did have a dilemma with an odd shape staircase that our child gate would not fit and a toddler but we just moved a couch to block the entry from the livingroom to the front area and that worked well. The home is tiled so it was easy to keep the floors clean. The beds were comfortable and the pillows were mixtures of full and flat to suit all preferences. The home smelled nice and did not have the mild moldy smell many FL homes can have from the high humidity in the area. The owners were a pleasure to work with, very accommodating, helpful and prompt to answer my silly questions about where items in the house were and how to work locks etc We will for sure stay here the next time we visit orlando area. This villa felt like home and was hard to leave. It truly is so comfortable and I am a hard one to please! If you are reading this and considering this home...seriously do not continue your search. There is so much that can go wrong when renting homes on vacations. But this one does everything right!

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$213

Amarula Estates, close to everything,in the heart of Daytona beach area.

Daytona Beach villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$1,009

Carpe Diem! Stunning FL Beach House ON Beach +Dock!

Stuart house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 8

“Perfect for a large family” This is house is fabulous, we had a group of 18 from ages 3-70 and everyone had an amazing time. The house if fully stocked with outside "everything" (pop-up, chairs, beach toys, water toys, masks, snorkles, water shoes....) you need for the beach, and then you go to the river side, and there are paddle boards and kayaks, and little beach with a fire pit, that made the 4th of July extra special. We saw a number of firework shows and made smores, hit will everyone in the group. This was the first time all 4 family's stayed in the same house, and there was plenty of space for everyone to hang out together, or get away from eachother if needed. The kitchen is also ready with plenty of pots, pans, spices, paper plates, plastic silverware, etc. We cooked all but one meal (kids wanted pizza delivered) for the large group with ease for the 5 days we were there. The washers and dryers also helped to make the trip perfect. Everyone was able to back light since we could wash and re-wear items, so no large suitcases needed for the trip.

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$251

5-star LUXURY RESORT:Tennis, Pool, Spa, 3 acre Estate near Beach, Golf, Races

Rancho Santa Fe house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$1,090

Home Away From Home Offers The Best Of Ahwatukee

Phoenix house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$247

Luxury Lakeside House with private solar heated pool and spa

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

“Very nice.” We had a great time. The house was clean, accommodations were very nice. The kitchen light started to burn out. One call & it was fixed quickly. We would go back.

Responds fast! avg. 3 hours 25 minutes

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$160

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$481

Swiss 45 - Swiss Waterski Villa

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$402

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$115

Villa Alamea - Yacht Club area - Luxury vacation home - boaters dream

Cape Coral villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“A wonderful place to spend a vacation!” We had a great time at Villa Alamea! The home is beautiful and has every amenity imaginable. We vacationed with 3 generations of family and enjoyed the pool and outdoor living space as well as the indoors. I would definitely recommend this home! The location was awesome as well.

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$860

Updated Villa with Pool & Spa Near Disney!

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Awesome” My wife and I stayed here and loved it. The house was clean and comfortable and had all the amenities needed for a vacation home that truly was a home away from home. The pool and spa were the perfect way to start and end the day after the parks and were very private with fencing and shrubs surrounding them. I've rented other homes in the area this was the best and I will definitely be coming back with the whole family. Excellent 5 stars

Responds fast! avg. 1 hour 17 minutes

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$155

Large Sunny Pool Home Near Disney and Golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“Very Good” Nice quite location. It is close to the theme parks and all the family attractions. My family is well pleased with the spacious home, The children and adults are taking full advantage of the pool throughout the entire day prior to leaving the house and upon our return.

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$182

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$1,720

Magical home built around Windmill with views of ocean

Centerville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$1,714

Disney, Universal, Beaches, Golf, New Rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$218

THE SANIBEL SUN CASTLE Luxury home, heated pool, great location, bike to beach

Sanibel Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$574

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$2,523

⭐⭐⭐Disney Contemporary 3 ⭐⭐⭐

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

“Cheerleading Comp” We had a great time and the house was more then we could ask for. There was so much room the beds were all very comfortable . The house was clean it ready for our stay on time. The pool was clean large area to sit and relax. The rooms were large and had lots of room for your things. The area is very quiet and close to everything. I will for sure rent this home again in the future and would recommend to friends and family.

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$281

3BR Luxury Villa Dolphino 5 Min Walk to the Beach! * 5 star *

Fort Lauderdale house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$574

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$263

UPSCALE 4BR BEACH HOUSE WITH POOL, HOT TUB & FIRE PIT-100 yards to the gulf

Pensacola Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

Responds fast! avg. 32 minutes

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$918

6 BDRM Estate w/Heated Pool-Spa-Volleyball ❤️ Best Golf-Dine-Shop Area.

Scottsdale house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 22

Responds fast! avg. 1 hour 11 minutes

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$224

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$986

“A Classy Vacation Experience in any Season” My brother, who has problems walking, and I stayed at Sunnybank for a little under a week in the early spring when the Corolla horses are foaling. The layout of the well-appointed, three-storey main building was perfect for our needs: the fabulous view from the top floor living room provided the inspiration for him to walk up the grand stair case, and he could take the elevator when he was having problems walking. (There are two bedrooms with walk-in showers to accommodate people who have a problem walking.) It rained the first two days, which might have been gloomy any where else, but the library of videos, and stashes of games and playing cards gave us the opportunity to connect in ways that we hadn't since we were children. The fabulous cook's kitchen and multiple eating areas can accommodate a wedding party, family reunion, or any get away time one might want. Mine was a working vacation and the office there, which is outfitted with excellent Ethernet and WiFi connections plus a daybed for napping, was a better arrangement than my office at home. Comfort and casual, yet classy ambience abounds at Sunnybank. An excellent find!

Responds fast! avg. 3 hours 13 minutes

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$1,145

Magnificent private Southampton Estate

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$5,160

LUXURY RENTALS ~ THE PIER HOUSE ~ BEACH VIEWS

Naples house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

“The pier house” Beautiful house... Super great location !!! Watched the fireworks from the top balcony... Best view in town !! Everything was perfect for the week!

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$1,865

BEST BEACH OCEANFRONT VIEWS! 5-STAR AMENITIES! Rated #1 Travel review SPECIALS!!

Orange Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

“Wonderful beach condo with amazing ocean views” I stayed at Audrey and Eric's condo during Hangout Music Fest, and it was a comfortable place to sleep, eat, get work done, and enjoy the view of the ocean. Checking in and out was hassle-free, as was communicating with the owners. Definitely a great spot for anyone looking to enjoy some time on the beach.

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$573

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

“Decent place but lacking in some areas” For one week in July 2014, my family from Alabama to Alaska (with us from Canada) all stayed at 928 Solona Circle. Overall we were happy with the house rental but do not stay here if you need assistance with anything. It took my 4 phone calls over 3 days to just find out what the Wi-Fi password had been changed to (the one that we were emailed was incorrect). It may not be the safest neighbourhood as there were police men in the gated area twice during our stay. And the house was filled with broken outlet covers and had very dirty couches, which needed steam cleaning. It was a spacious home and we loved the walk-in closets as well as the ease in which to find it and the easy drive to Disneyworld. But if you want to stray there, you need to supply everything- even your own toilet paper and Kleenex. The jets ion eth hot tub did not work and the game room had a broken foosball table. Overall we were mainly happy with our stay but were disappointed with a few things.

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$190

MyLBIBeachRental, 6 from Beach, 6 Bedroom, Sleeps 12, New Construction in 2023

Beach Haven house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$3,434

Villa by the sea with salt water pool for dreaming

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$229

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$293

Groovy Mouse House with private pool near Disney

Reunion villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$402

Match: Private outdoor pool (heated) Solarium or roof terrace

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Price per night from

$279

Viewing 38 of 9,279
rentals in Kailua

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