Summer Getaways with SunSki Resorts

SunSki Resorts offers a diverse array of summer vacation rentals to suit every style and budget. Revel in the comfort of amenities such as swimming pools, hot tubs, and fast WiFi while you explore your destination. Whether booking a weekend getaway or a long-term stay, including monthly rentals, our accommodations welcome families, groups, reunions, weddings, friends, and even pets. Experience the pinnacle of summer travel with SunSki Resorts.

About Summer
SunSki Resorts > Summer Rentals

Most Popular Places for Summer Rentals

Explore the most popular destinations for summer rentals, from sunny beaches to countryside retreats ideal for warm-weather travel. Summer stays support outdoor activities and relaxation. These destinations are favorites for seasonal holidays and family trips.

Kissimmee Summer Rentals22309+ properties West Kissimmee Summer Rentals18552+ properties Four Corners Summer Rentals17641+ properties Davenport Summer Rentals17225+ properties Sevierville Summer Rentals16485+ properties Westerland Summer Rentals15009+ properties Downtown Dubai Summer Rentals13281+ properties Myrtle Beach Summer Rentals11949+ properties Bibione Summer Rentals9633+ properties Zingst Summer Rentals9314+ properties Florida Central Atlantic Coast Summer Rentals9220+ properties Dubai Marina Summer Rentals9125+ properties

Other Popular Summer Rentals Destinations

Find popular summer rental destinations perfect for beach holidays, outdoor adventures, and warm-weather travel. Ideal for soaking up the sun and enjoying seasonal attractions.

Australia

Canada

Europe

USA

Best Summer Rentals in Kissimmee

Discover premium Summer Rental in Kissimmee, crafted for travelers seeking comfort, style, and privacy throughout their journey. Each Summer Rental features a thoughtfully designed interior and carefully chosen amenities that elevate the stay experience beyond the ordinary. Enjoy spacious layouts, refined design, and the flexibility of a private Summer Rental that offers both relaxation and independence, perfect for travelers who value quality, space, and a stay that feels truly special.

10.0
Exceptional
(4 Reviews)
Summer Bay Resort 2br suite, Saturday check-in
1100 ft² 8 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $119/Night For 7 Nights US $835
View Deal
10.0
Exceptional
(22 Reviews)
Incredible 6BR Villa by Disney Private Pool Games
3756.6 ft² 15 Guests 6 Bedrooms 6 Bathrooms
Family Friendly House
  • Spa
  • Fireplace/Heating
  • Pool
US $474/Night For 7 Nights US $3,317
View Deal
New
Family Condo Near Disney w Pool & Gym—Pets Welcome
1288 ft² 7 Guests 3 Bedrooms 2 Bathrooms
Ocean View Condo
  • Hot Tub
  • Spa
  • Fireplace/Heating
US $264/Night For 7 Nights US $1,848
View Deal
10.0
Exceptional
(1 Review)
Summer Bay Resort 1br suite, Saturday check-in
823 ft² 4 Guests 1 Bedroom 1 Bathroom
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $109/Night For 7 Nights US $761
View Deal
10.0
Exceptional
(13 Reviews)
Affordable Luxury Home Near Walt Disney World - Sunshine Villa at Glenbrook Resort, Orlando, Florida
1948.27 ft² 8 Guests 4 Bedrooms 4 Bathrooms
House
  • Oceanfront
  • Hot Tub
  • Fireplace/Heating
US $129/Night For 7 Nights US $903
View Deal
10.0
Exceptional
(1 Review)
Summer Bay Resort 2br suite, Sunday check-in
1100 ft² 8 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $109/Night For 7 Nights US $761
View Deal
9.8
Exceptional
(6 Reviews)
South Facing Pool & Spa- 2 Master Bedrooms
1963 ft² 10 Guests 1 Bedroom 3 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
US $223/Night For 7 Nights US $1,563
View Deal
9.2
Exceptional
(5 Reviews)
3 Bedroom Villa with Poolside Cinema and Games Room Close to theme Parks sleeps 6
1432 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Private Pool
  • Fireplace/Heating
  • Pool
US $246/Night For 7 Nights US $1,721
View Deal
New
Cozy cabin in cool Clermont with WiFi, AC
4 Guests 1 Bedroom 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Air Conditioner
  • Internet
US $383/Night For 7 Nights US $2,681
View Deal
See More Kissimmee Summer Rentals

Luxury Places to Stay in Kissimmee

Discover luxury places to stay in Kissimmee, offering refined comfort, premium amenities, and spacious accommodations designed for an elevated travel experience. These properties feature elegant interiors, high-end facilities, and attentive service. Perfect for romantic getaways, business trips, and special occasions. Travelers choose these stays for exclusive locations, exceptional comfort, and memorable experiences.

10.0
Exceptional
(1 Review)
6 Bed villa close to disney
3378 ft² 12 Guests 6 Bedrooms 6 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Kitchen
Unlock the Best Price
View Deal
8.0
Excellent
(2 Reviews)
BRAND NEW Storey Lake- 5 bedrooms, 5 bathrooms, private pool - Harry Potter & Minions theme
3000 ft² 14 Guests 5 Bedrooms 5 Bathrooms
Family Friendly Villa
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
Unlock the Best Price
View Deal
8.8
Fabulous
(3 Reviews)
BRAND NEW Solara Resort - 5 bedrooms, Private Pool - FROZEN & HARRY POTTER Themed Rooms
2400 ft² 12 Guests 5 Bedrooms 5 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
Unlock the Best Price
View Deal
8.8
Fabulous
(11 Reviews)
Storey Lake BRAND NEW - 6 Bedrooms, Private Pool, Themed Bedrooms
3100 ft² 17 Guests 6 Bedrooms 5 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
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View Deal
New
Solara Resort - 5 bedrooms, Private Pool - FROZEN & HARRY POTTER - DISNEY AREA
12 Guests 5 Bedrooms 5 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
Unlock the Best Price
View Deal
New
FROZEN & HARRY POTTER Themed Rooms * Solara Resort - 5 bedrooms, Private Pool
12 Guests 5 Bedrooms 5 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
Unlock the Best Price
View Deal
10.0
Exceptional
(58 Reviews)
⭐️ The Mediterranean Villa Orlando 😀 DISNEY ⭐️ Private Pool & Games Room
5201 ft² 12 Guests 5 Bedrooms 5 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Hot Tub
Unlock the Best Price
View Deal
8.0
Excellent
(1 Review)
Thanksgiving for a family of 8 in Celebration at Mystic Dunes Resort & Golf
8 Guests 2 Bathrooms
Resort
  • Hot Tub
  • Pool
  • Air Conditioner
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New
Elegant Townhouse near Disney with Resort & Waterpark Access - 768DR
1704 ft² 2 Bathrooms
Family Friendly Hotel
  • Hot Tub
  • Fireplace/Heating
  • Pool
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View Deal
See More Kissimmee Luxury Rentals

Top-Rated Vacation Rentals with a Pool in Kissimmee

Explore top-rated vacation rentals with pools in Kissimmee, selected for quality, guest satisfaction, and relaxing poolside experiences. They offer private or shared pools, sunbathing areas, and modern amenities. Ideal for families, friends, or extended stays. Guests enjoy convenience, safety, and proximity to local attractions while relaxing by the water.

10.0
Exceptional
(371 Reviews)
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
3534 ft² 14 Guests 6 Bedrooms 4 Bathrooms
Ocean View House
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
US $473/Night For 7 Nights US $3,313
View Deal
10.0
Exceptional
(321 Reviews)
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
1450 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Family Friendly Villa
  • Hot Tub
  • Spa
  • Fireplace/Heating
US $174/Night For 7 Nights US $1,216
View Deal
10.0
Exceptional
(317 Reviews)
Water View - Pool & Spa - 3.5 miles to Disney - BBQ
1800 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
US $249/Night For 7 Nights US $1,741
View Deal
10.0
Exceptional
(312 Reviews)
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Condo
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $235/Night For 7 Nights US $1,648
View Deal
10.0
Exceptional
(278 Reviews)
Amazing villa close to Disney with 5* Reviews
2931 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
US $282/Night For 7 Nights US $1,975
View Deal
10.0
Exceptional
(263 Reviews)
Quiet, Clean, Disney-3.5 miles, Well kept home! Free Pool/spa Heat!
1800 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Family Friendly House
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
US $255/Night For 7 Nights US $1,788
View Deal
10.0
Exceptional
(261 Reviews)
Conservation View - Hot Tub - Free Pool Heat - Very Private
2000 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Ocean View Villa
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
US $260/Night For 7 Nights US $1,820
View Deal
10.0
Exceptional
(259 Reviews)
BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED
1797 ft² 8 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Fireplace/Heating
  • Pool
  • Ocean View
US $159/Night For 7 Nights US $1,112
View Deal
10.0
Exceptional
(255 Reviews)
Our DisneyDreamVilla - minutes to DisneyWorld!
2500 ft² 11 Guests 5 Bedrooms 5 Bathrooms
Ocean View Villa
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
US $382/Night For 7 Nights US $2,675
View Deal
See More Kissimmee Rentals with Pools

Pet-Friendly Vacation Rentals in Kissimmee

Find pet-friendly vacation rentals in Kissimmee, providing comfortable, welcoming stays for travelers who want to bring their pets along. These accommodations include pet-friendly spaces, walking areas, and supportive services. Perfect for guests who do not want to leave their pets behind. Families and travelers enjoy flexibility, peace of mind, and inclusive experiences for all.

10.0
Exceptional
(1 Review)
Luxury Disney Retreat Heated Pool & Jacuzzi-7895
15 Guests 6 Bedrooms 5 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $753/Night For 7 Nights US $5,273
View Deal
10.0
Exceptional
(8 Reviews)
Amazing 8br w pool theater game room by Disney
4305.56 ft² 21 Guests 1 Bedroom 5 Bathrooms
Family Friendly Villa
  • Fireplace/Heating
  • Pool
  • Pet Friendly
US $528/Night For 7 Nights US $3,696
View Deal
10.0
Exceptional
(2 Reviews)
Willow Bend
1 Bedroom 1 Bathroom
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $632/Night For 7 Nights US $4,427
View Deal
10.0
Exceptional
(1 Review)
Lovely Pool House in Kissimmee
8 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $296/Night For 7 Nights US $2,074
View Deal
10.0
Exceptional
(7 Reviews)
Mufasa's Pride
2185.07 ft² 10 Guests 5 Bedrooms 4 Bathrooms
House
  • Oceanfront
  • Fireplace/Heating
  • Pool
US $224/Night For 7 Nights US $1,567
View Deal
10.0
Exceptional
(1 Review)
Family-Friendly 4BR Townhouse with Private Pool at Storey Lake Resort – Near Disney
1914 ft² 11 Guests 4 Bedrooms 3 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
US $272/Night For 7 Nights US $1,902
View Deal
10.0
Exceptional
(1 Review)
Cozy 2-bedroom apartment at WESTGATE VACATION VILLAS RESORT near DISNEY WORLD
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $244/Night For 7 Nights US $1,708
View Deal
6.0
Good
(1 Review)
AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY AND SEAWORLD
4 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $142/Night For 7 Nights US $993
View Deal
New
Vibrant Island Getaway with Private Pool Near Disney with Margaritaville Resort.
4480 ft² 18 Guests 8 Bedrooms 9 Bathrooms
Ocean View Cottage
  • Private Pool
  • Fireplace/Heating
  • Pool
US $1,415/Night For 7 Nights US $9,902
View Deal
See More Kissimmee Pet Friendly Rentals

Summer Rentals FAQs

What is the most popular destination for a Summer Rental?

Kissimmee is a highly sought-after destination for Summer Rentals, offering over 22309+ options. Visitors love this location for its variety, convenience, and unforgettable experiences.

How do I ensure the Summer Rental meets my needs?

Review the description, photos, and verified guest reviews carefully. For specific requirements, you can contact the provider directly to ensure the Summer Rental is right for you.

How can I communicate special requests for a Summer Rental?

Use the platform’s messaging system to reach out to the owner or provider. This allows you to ask questions and discuss any special requests before your trip.

What should I do if I need to modify or cancel my Summer Rental booking?

Modifications and cancellations are usually handled through our partners. Policies vary by listing or activity, so check the specific terms for your Summer Rental through our partners. Please visit the partner’s website with whom you booked.

Are there different price ranges available for Summer Rentals?

Yes, Summer Rentals are available for various budgets. Use the price filter to find options that match your financial preferences while still offering quality experiences.