
Vacation rentals with a pool in Upper Prince's Quarter
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Upper Prince's Quarter
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Upper Prince's Quarter rentals with a pool
House rentals with a pool

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

Welcome to a slice of paradise!

Villa close to the beach

New-Sunset Place Villa w Stunning Waterfront Views

Slowlife - Villa Wellness 4 beds

The best view on the island!

2 Bedroom Ocean Front Villa, Private Infinity Pool

Villa Monchal, 1-minute walk to the beach
Condo rentals with a pool

Comfort & Charm – Premium Studio

Oceanfront w Pool | Maho Beach area

"SeaBird" studio, feet in the water on the beach

Beachfront Condo| Pool View + Private Beach Access

New studio with superb view of the Caribbean Sea

Baie Orientale Cosy Duplex 1

Seneca Condo

Sint Maarten La Terrasse Maho
Other vacation rentals with a pool

Ultra Modern Tropical Villa with stunning sea view

Oceanfront Guana Bay Villa with View of St. Barts

magnificent Orient Bay sea view apartment

Villa MEWE. Sea view 3 bedrooms

C342 - Glorious Lagoon View Apartment with Balcony

Villa Indigo Dream, Indigo Bay SXM

Villa Tibo

Cozy Cabanita, in lush tropical garden with pool
Quick stats about vacation rentals with a pool in Upper Prince's Quarter
Total rentals
380 properties
Total number of reviews
2.5K reviews
Family-friendly rentals
300 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
200 properties have a dedicated workspace
Wifi availability
370 properties include access to wifi
Destinations to explore
- Rentals with a patio Upper Prince's Quarter
- House rentals Upper Prince's Quarter
- Waterfront rentals Upper Prince's Quarter
- Rentals with a washer and dryer Upper Prince's Quarter
- Villa rentals Upper Prince's Quarter
- Pet-friendly rentals Upper Prince's Quarter
- Beachfront rentals Upper Prince's Quarter
- Rentals with outdoor seating Upper Prince's Quarter
- Rentals with breakfast Upper Prince's Quarter
- Smoking-friendly rentals Upper Prince's Quarter
- Apartment rentals Upper Prince's Quarter
- Family-friendly rentals Upper Prince's Quarter
- Rentals with beach access Upper Prince's Quarter
- Condo rentals Upper Prince's Quarter
- Rentals with a hot tub Upper Prince's Quarter
- Serviced apartment rentals Upper Prince's Quarter
- Fitness-friendly rentals Upper Prince's Quarter
- Rentals with pools Sint Maarten
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes