10801+ Vacation Rentals & Holiday Homes in Cypress Pointe |
Cypress Pointe Accommodations - Hotels & Rentals
Villa
10.0Exceptional
(20 Reviews)
4 Bedrooms
4 Baths
8 Guests
2195.84 ft²
Oceanfront
Spa
Fireplace/Heating
Pool
US $177/Night
7 Nights - US $1,237
House
- Orlando
- ·
- Bridgewater Crossing
- 0.10 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
Private Pool- Fireplace/Heating
- Pool
Balcony/Terrace
US $630/Night
7 Nights - US $4,409
Villa
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $174/Night
7 Nights - US $1,218
House
10.0Exceptional
(10 Reviews)
5 Bedrooms
4 Baths
13 Guests
10763.91 ft²
- Oceanfront
- Fireplace/Heating
- Pool
Ocean View
US $267/Night
7 Nights - US $1,871
House
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
Kitchen
Parking
US $222/Night
7 Nights - US $1,554
House
- Orlando
- ·
- West Kissimmee
- 3.35 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
5 Baths
14 Guests
3003.13 ft²
- Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $387/Night
7 Nights - US $2,709
House
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Parking
Internet
US $784/Night
7 Nights - US $5,485
House
10.0Exceptional
(6 Reviews)
5 Bedrooms
8 Baths
10 Guests
4144.11 ft²
- Pool
- Balcony/Terrace
Pet Friendly- Kitchen
US $382/Night
7 Nights - US $2,674
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $370/Night
7 Nights - US $2,587
Luxury Places to Stay in Cypress Pointe
Over 10000+ Luxury Places to Stay in or Near Cypress Pointe
Villa
10.0Exceptional
(58 Reviews)
5 Bedrooms
5 Baths
12 Guests
5201 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Unlock the Best Price
House
5 Bedrooms
4 Baths
10 Guests
- Pool
- Parking
Air Conditioner- Internet
US $8,969/Night
7 Nights - US $62,783
House
6 Bedrooms
5 Baths
10 Guests
- Hot Tub
- Pool
- Parking
- Air Conditioner
US $8,087/Night
7 Nights - US $56,609
House
Eagle Cove - Private Pool, Sports Court, Sauna, Game Room, Theater, Bowling Alley, Gym, Themed Rooms
8.0Excellent
(13 Reviews)
14 Bedrooms
17 Baths
36 Guests
21397 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $7,612/Night
7 Nights - US $53,284
House
5 Bedrooms
3 Baths
12 Guests
1937.5 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $7,567/Night
7 Nights - US $52,967
House
14 Bedrooms
11 Baths
30 Guests
6257 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $7,539/Night
7 Nights - US $52,776
House
12 Bedrooms
13 Baths
46 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $7,412/Night
7 Nights - US $51,881
House
16 Bedrooms
22 Baths
68 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $6,867/Night
7 Nights - US $48,071
Villa
- Orlando
- ·
- Four Corners
- 4.51 mi to center
12 Bedrooms
15 Baths
46 Guests
16000 ft²
- Fireplace/Heating
- Pool
Breakfast- Kitchen
US $6,629/Night
7 Nights - US $46,405
Top-Rated Vacation Rentals with a Pool in Cypress Pointe
Over 9204+ Top-Rated Vacation Rentals with a Pool in or Near Cypress Pointe
Villa
- Orlando
- ·
- Sunridge Woods
- 0.19 mi to center
10.0Exceptional
(189 Reviews)
4 Bedrooms
2 Baths
8 Guests
1800 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $239/Night
7 Nights - US $1,676
House
10.0Exceptional
(142 Reviews)
4 Bedrooms
2 Baths
8 Guests
1695 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $182/Night
7 Nights - US $1,271
Condo
10.0Exceptional
(136 Reviews)
2 Bedrooms
2 Baths
4 Guests
1260 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $129/Night
7 Nights - US $902
House
10.0Exceptional
(127 Reviews)
5 Bedrooms
7 Baths
12 Guests
5300 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $800/Night
7 Nights - US $5,597
Villa
- Orlando
- ·
- Grand Reserve
- 0.16 mi to center
10.0Exceptional
(126 Reviews)
5 Bedrooms
3 Baths
10 Guests
2800 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $231/Night
7 Nights - US $1,615
House
10.0Exceptional
(124 Reviews)
3 Bedrooms
4 Baths
8 Guests
2228 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $283/Night
7 Nights - US $1,980
House
10.0Exceptional
(123 Reviews)
6 Bedrooms
5 Baths
14 Guests
3300 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $327/Night
7 Nights - US $2,292
House
10.0Exceptional
(122 Reviews)
13 Bedrooms
12 Baths
33 Guests
6500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,504/Night
7 Nights - US $10,531
House
- Orlando
- ·
- Loma Linda
- 0.17 mi to center
10.0Exceptional
(118 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $165/Night
7 Nights - US $1,158
Pet-Friendly Vacation Rentals in Cypress Pointe
Over 1525+ Pet-Friendly Vacation Rentals in or Near Cypress Pointe
Villa
10.0Exceptional
(4 Reviews)
5 Bedrooms
3 Baths
10 Guests
1679.17 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $189/Night
7 Nights - US $1,323
House
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $965/Night
7 Nights - US $6,753
House
- Orlando
- ·
- Cypress Pointe
- 0.12 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $668/Night
7 Nights - US $4,676
Villa
10.0Exceptional
(4 Reviews)
5 Bedrooms
5 Baths
10 Guests
1776.05 ft²
- Hot Tub
- Fireplace/Heating
- Pool
View
US $157/Night
7 Nights - US $1,099
House
8.6Fabulous
(4 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $912/Night
7 Nights - US $6,386
House
10.0Exceptional
(2 Reviews)
7 Bedrooms
5 Baths
18 Guests
3627.44 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
US $592/Night
7 Nights - US $4,144
House
8.0Excellent
(17 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $241/Night
7 Nights - US $1,687
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
5 Baths
13 Guests
2281.95 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $314/Night
7 Nights - US $2,198
House
- Orlando
- ·
- West Kissimmee
- 3.20 mi to center
8.0Excellent
(2 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
- Pet Friendly
- Parking
- Internet
US $749/Night
7 Nights - US $5,244
Large Vacation Homes & Villas in Cypress Pointe
Over 7728+ Large Vacation Homes & Villas in or Near Cypress Pointe
Villa
10.0Exceptional
(4 Reviews)
3 Bedrooms
4 Baths
6 Guests
2077.43 ft²
- Pool
- Balcony/Terrace
- Parking
- Air Conditioner
US $295/Night
7 Nights - US $2,065
Villa
- Orlando
- ·
- Sandy Ridge
- 0.18 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Spa
- Fireplace/Heating
- Pool
US $179/Night
7 Nights - US $1,253
Villa
- Orlando
- ·
- Windwood Bay
- 0.21 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $824/Night
7 Nights - US $5,768
House
10.0Exceptional
(4 Reviews)
5 Bedrooms
5 Baths
13 Guests
2723.27 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
US $689/Night
7 Nights - US $4,824
Villa
7.0Very Good
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Kitchen
- Parking
- Internet
US $170/Night
7 Nights - US $1,189
House
10.0Exceptional
(4 Reviews)
5 Bedrooms
4 Baths
20 Guests
96.88 ft²
- Pool
- View
- Parking
- Air Conditioner
US $355/Night
7 Nights - US $2,485
House
- Orlando
- ·
- West Kissimmee
- 3.23 mi to center
6.4Good
(120 Reviews)
1 Bedroom
1 Bath
14 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $813/Night
7 Nights - US $5,691
House
10.0Exceptional
(3 Reviews)
1 Bedroom
5 Baths
10 Guests
2077.43 ft²
- Fireplace/Heating
- Pool
- View
- Parking
US $371/Night
7 Nights - US $2,599
House
6.4Good
(21 Reviews)
5 Bedrooms
1 Bath
11 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $494/Night
7 Nights - US $3,458
Wheelchair Accessible Vacation Homes in Cypress Pointe
Over 863+ Wheelchair Accessible Vacation Homes in or Near Cypress Pointe
House
10.0Exceptional
(1 Review)
4 Bedrooms
6 Baths
8 Guests
2798.62 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $637/Night
7 Nights - US $4,460
Villa
5.0Average
(2 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $197/Night
7 Nights - US $1,379
House
- Orlando
- ·
- Bridgewater at Town Center
- 0.03 mi to center
8.6Fabulous
(49 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $500/Night
7 Nights - US $3,500
House
- Orlando
- ·
- West Kissimmee
- 3.44 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
12 Guests
2400.35 ft²
- Pool
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $189/Night
7 Nights - US $1,323
Condo
- Orlando
- ·
- Four Corners
- 4.99 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
- Pool
- Pet Friendly
- Parking
- Internet
US $575/Night
7 Nights - US $4,024
House
10.0Exceptional
(1 Review)
6 Bedrooms
4 Baths
18 Guests
34186.18 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $325/Night
7 Nights - US $2,277
Villa
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Kitchen
- Internet
US $523/Night
7 Nights - US $3,664
Villa
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $130/Night
7 Nights - US $910
Resort
9.4Exceptional
(625 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $339/Night
7 Nights - US $2,373
Cypress Pointe Varoom and Airbnb Places to Stay Under $200
Over 1985+ Cypress Pointe Varoom and Airbnb Places to Stay Under $200
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
8180.57 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $98/Night
7 Nights - US $685
House
7.8Very Good
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $123/Night
7 Nights - US $862
House
- Orlando
- ·
- Windwood Bay
- 0.25 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $184/Night
7 Nights - US $1,286
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
1905.21 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $150/Night
7 Nights - US $1,052
House
7.2Very Good
(36 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $105/Night
7 Nights - US $735
Apartment
- Orlando
- ·
- Four Corners
- 5.13 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
1969.8 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $145/Night
7 Nights - US $1,014
House
7.0Very Good
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $124/Night
7 Nights - US $870
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1603.82 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $140/Night
7 Nights - US $978
House
- Orlando
- ·
- Four Corners
- 5.22 mi to center
6.2Good
(109 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $164/Night
7 Nights - US $1,148
Instantly Bookable Vacation Homes in Cypress Pointe
Over 6886+ Instantly Bookable Vacation Homes in or Near Cypress Pointe
House
6 Bedrooms
5 Baths
12 Guests
4004.17 ft²
- Pool
- Balcony/Terrace
- Child Friendly
Laundry
US $341/Night
7 Nights - US $2,387
Villa
10.0Exceptional
(5 Reviews)
6 Bedrooms
5 Baths
14 Guests
4392 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $468/Night
7 Nights - US $3,275
Condo
- Orlando
- ·
- Four Corners
- 5.15 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $84/Night
7 Nights - US $585
House
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
10 Guests
3367 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
US $295/Night
7 Nights - US $2,065
House
8.0Excellent
(1 Review)
7 Bedrooms
5 Baths
16 Guests
3137 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
US $280/Night
7 Nights - US $1,962
House
12 Bedrooms
11 Baths
28 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $830/Night
7 Nights - US $5,808
House
- Orlando
- ·
- Paradise Woods
- 0.06 mi to center
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $341/Night
7 Nights - US $2,385
House
3 Bedrooms
3 Baths
8 Guests
1307 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $728/Night
7 Nights - US $5,096
House
- Orlando
- ·
- West Kissimmee
- 3.19 mi to center
10 Bedrooms
10 Baths
24 Guests
4707 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $605/Night
7 Nights - US $4,235
Book a Last Minute Place to Stay in Cypress Pointe
About Cypress Pointe Vacation Rentals
Discover More than 10801 Incredible Getaway Rentals Available in Cypress Pointe. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Cypress Pointe.
Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Cypress Pointe, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Cypress Pointe. The Average Size of Places to Stay Near Cypress Pointe is 2334.58 ft², with Prices Averaging US $492 per Night.
Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Cypress Pointe. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.
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Top Hotels & Vacation Rentals in Cypress Pointe
| Type | Count |
|---|---|
| Vacation Homes | 7001 |
| Villas | 2142 |
| Holiday Apartments | 582 |
| Cottages | 39 |
Use these Quick Filters to Find a Vacation Rental in Cypress Pointe
★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Cypress Pointe with Online Reservations.
Weather in Cypress Pointe, FL
View the weather forecast for Cypress Pointe before booking your Cypress Pointe Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Cypress Pointe?
What are the top hotels, lake houses & vacation rentals in Cypress Pointe?
We provide an array of great vacation destinations in Cypress Pointe. If you are looking to stay in or around the Cypress Pointe area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Cypress Pointe:
- Adventure Villa - WOW Pool & SPA - All Vacation Themed + Beauty & Beast Dining
- Luxurious & Superb 3bd Reunion Townhome. Close to Disney!
- Get away from it all in a place that's close to it ALL! Renovated - near Disney!
- 5 Bedroom Beverly Hills 5300 sq ft in Reunion, Huge Pool, Reunion Amenities!
- 5BR Executive Villa Large Pool Gated Community in Championsgate area near Disney
- Reunion South facing pool home 3 bed/3.5 baths
- Spacious 6BR Family Retreat w/Private Pool and Spa in Resort Community!
- Access to 3 Private GOLF COURSES+2 Waterparks+POOL & SPA+Gameroom+THEATER+Disney
- Salt Water Pool, Convenient to Disney, Universal, Golf, Restaurants, Shopping
- Access to 3 Private GOLF COURSES+2 Waterparks+POOL & SPA+Gameroom+THEATER+Disney
How many Hotels & Vacation Rentals have private pools in Cypress Pointe?
We have 5866 Hotels & Vacation Rentals featuring a private pool in and near Cypress Pointe. Some of the best destinations to stay that feature or have access to a swimming pool are:
- Resort Perks & Gas Grill: Spacious Davenport Haven
- Anchor Cove Villa
- Crofton Springs House 4 Bedroom
- 7500 Marker av
Which hotel, lake house, or vacation rental in Cypress Pointe is best for families?
Searching for a family-friendly getaway in Cypress Pointe? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
- Modern 3Bd End Unit with Garage & Water View 7904
- Gorgeous Single Home With Private Pool at Encore
- Crofton Springs House 4 Bedroom
How many hotels, resorts, or rentals are available in Cypress Pointe?
Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 10801 in the Cypress Pointe area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Cypress Pointe.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Thousand Oaks Vacation Rentals in Orlando, Florida | 25 |
People Also Ask
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