Flag Hill, Saint Thomas Rentals with Pools

Updating...

age 0-16
232 Results

Relevance

Price: low to high

Price: high to low

Reviews

232 rentals in Flag Hill, Saint Thomas with pools

Great rentals within 20 miles that match your search

Starvilla--Walk to Cruz Bay!

Cruz Bay house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Swimming pool

All filters match

Price per night from

$487

Rare Brand New Luxury Beachfront Villa

East End condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$654

An Enchanting Caribbean Interlude affordable 4 you

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$166

"Suite Papaya"

Coral Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Swimming pool

All filters match

Price per night from

$413

Newly refurbished Longview Villa with Heated 40ft pool and stunning views

West End villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$572

Villa Madeira

St. John villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$600

Stunning Newly Renovated 1BR Beachfront Condo

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$573

Christian Villa

St Thomas Central villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,203

Antillean Yacht Charters

Water Island yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$1,649

⛵ Sail charter Catamaran NEW! Caribbean BVI's

Brewers Bay yacht

  • 1 bedroom
  • 3 bathrooms
  • sleeps 2

Match: Swimming pool

All filters match

Price per night from

$2,289

Captain's Quarters Inviting YOU to make Memories in Paradise

North Side apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Swimming pool

All filters match

Price per night from

$247

Sapphire Beach Front (Fully Renovated)

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$457

Beauty, Comfort, Value! Your Home in the Caribbean

St Thomas East townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$542

Beautiful 2 Bedroom Home with Pool, view Ocean

Charlotte Amalie villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$572

Villa Nautilus, East End, St. Thomas

East End condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 20 minutes

Match: Swimming pool

All filters match

Price per night from

$430

Luxury Villa with Large Pool Above Honeymoon Beach

Water Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$492

Escape Winter at Westin St. John Resort, USVI

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Swimming pool

All filters match

Price per night from

$2,004

Rare Brand New Luxury 2BR Beachfront 2FL condo

East End apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$737

Swogjan's Dragon 7A Carolina

Coral Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$400

Match: Swimming pool

All filters match

Price per night from

$217

Starfish Studio on Crystal Cove Sapphire Beach

Smith Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

All filters match

Price per night from

$224

Charming luxury villa/ Super views/ Sleeps 2-8

St. John house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“My happy place” A beautiful and well maintained villa with a breathtaking view of Coral Bay and the Francis Drake channel. Not the hustle and bustle of Cruz Bay but still close to great restaurants in Coral Bay. Separate living and sleeping buildings isa great idea.

Match: Swimming pool

All filters match

Price per night from

$542

Coconuts: Panoramic ocean views and sunsets

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Swimming pool

All filters match

Price per night from

$458

Sweet Wind Villa overlooking Hurricane Hole

Coral Bay house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Sweet Wind is outstanding” We just returned from 9 wonderful days at Nina"s Sweet Wind Villa. The view is spectacular, the trade winds always kept the villa very comfortable and the location to great snorkeling and beautiful beaches is a big plus. Nina is a great hostess and close by if you need any hints on where to go or places to eat but she is never in the way. She even was so kind to fillet a Mahi Mahi I bought in Cruz Bay!! The "Pod" set up of the Villa makes it really nice. The living, dinning and kitchen area is separate but right next to two pods that are the sleeping and bathroom areas. Great for 3 couples or a family. The East end of the Island is also very peaceful and quiet. We certainly plan to return.

Match: Swimming pool

All filters match

Price per night from

$686

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

All filters match

Price per night from

$1,799

“We didn't want to leave!” My husband and I stayed at Mooncottage for too short a time in april 2014. We loved it and will hope to go back one day. The layout of the cottage is perfect for a couple. Separate sleeping cottage allows for one to sleep-in undisturbed while the other makes coffee. The island/asian decor is very attractive and the house was fully equipped with everything we needed. But the very best feature is the view which is absolutely to die for. Once there, you will be happy to skip a day at the beach and just bask in the breezy air, taking an occasional dip in the tiny pool, positioned perfectly between the bedroom and the deck. The drive in is pretty hair-raising, but once you get the hang of the very steep and very rough roads (typical in Carol Bay and much of St. John) and the perilously steep driveway, you'll be so glad you made the journey!

Match: Swimming pool

All filters match

Price per night from

$818

Poi Pu St John Villa - great views & total privacy

Cruz Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“St John is just the best little island around.” The villa is wide open, very spacious. Open the big doors and you let the cool breezes in. There are always breezes at Poi Pu. It's great to have your own pool right there, even if you have spent the day at the beach. It's close to town for shopping and dinning, but there is nothing like dinning right there on the deck with the breezes and all those stars. I will be going back it's just the best place to be with friends. Carol

Match: Swimming pool

All filters match

Price per night from

$395

“Absolute Paradise!!!!” Thanks to Tom we had the perfect getaway!!! Fast booking, we were provided with tons of information before we even left and the deposit returned asap. This condo was in the best place - you were in your own world yet so close to everything. We had privacy, everyone was pleasant and perfect weather. All that was needed was right there. The view was beautiful, the pool 2 minutes away - walking and Sapphire Beach 5 minutes away - walking. And lets not leave out the Off the Grid food truck at the top of the hill. We are early risers so we snorkeled in the morning, walked the beach in the afternoon and made good use of the pool 7am to 10pm with cocktails and appetizers at the Sapphire and Grill. The ferry to St. Thomas is a 5 minute drive too!!! This is the place you want to be and we will definitely be booking this amazing place again. Thanks to you Tom and your condo - you rock!!!!

Responds fast! avg. 3 hours 18 minutes

Match: Swimming pool

All filters match

Price per night from

$160

VILLA AMOUR ,Romantic , Art Lovers Paradise ,

North Side villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Perfect!” Title says it all. PERFECT island vacation home. Better than advertised. We had 7 adults and 2 infants and had plenty of room to relax. Pool, views are incredible. Convenient enough to travel the rest of the island (although you may ask yourself "why leave!". Rick and Steve are great hosts, responsive to any questions you might have. Recommend renting SUV and also that you give yourself plenty of time at the airport when departing. Highly recommend Villa Amour and would definitely return!

Responds fast! avg. 1 hour 0 minutes

Match: Swimming pool

All filters match

Price per night from

$802

Waterfront Escape: Paradise at a Great Price!

East End studio

  • Studio
  • 1 bathroom
  • sleeps 4

“Amazing Experience” I loved my stay at this condo! Great location! Owner was super friendly and helpful. The condo was very clean and newly renovated, exactly like the photos shows. I could have not asked for a better vacation. Will definitely come back again.

Match: Swimming pool

All filters match

Price per night from

$315

Sapphire 1 Bedroom-Free H/S WIFI & No Excessive Owner Fees #257

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$205

Drake's View: Voted Best View in the Caribbean

Coral Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Awesome family vacation” This was our second visit to Drakes View and we again enjoyed everything the property has to offer...views, a well equpped kitchen, hot tub and ample space for our 3 generations to be together for Thanksgiving week. In spite of an abnormally rainy week, we made the best of our beach time and enjoyed the views from the villa when we were forced inside. We lovedbeing able to stay overlooking Coral Bay,our favorite side of St. Johns. We explored several new beaches and snorkeling apots. Thanks to the Roberts family and their wonderful concierge team of Dorothy and Fernando.

Match: Swimming pool

All filters match

Price per night from

$911

Sea Dreams St Thomas Villa near beach with pool

Charlotte Amalie house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Peace and privacy with warm, caring hosts!” Peace, privacy and real attention from hosts Joyce and Nick Bailey at their secluded guesthouse---"a place where everyone knows your name." For those fortunate enough to book here, you will find a comfy, airy two-story guesthouse with extraordinary views over the Caribbean, a great pool for lounging, terrific jogging and walking opportunities, a first-rate nearby restaurant and all the comforts of home. A little jewel for families with kids, couples traveling together and older vacationers who like an acive outdoors life.

Match: Swimming pool

All filters match

Price per night from

$590

Beachfront Villa with a Down Island View-Priceless

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

“Well maintained, quality furnished condo with very helpful owner.” We have stayed in several different condos @ Sapphire Beach in several different price ranges. John's is by far the best maintained despite it not being the highest end priced. It also has a great bar/eating area on the lower deck. Renting from John is like renting from a friend or family member. There were no surprises from John other than I had over paid without realizing & he contacted me to let me know he was sending me a check.

Match: Swimming pool

All filters match

Price per night from

$401

Spectacular Sunsets & Ocean Views Remodeled Villa

Cruz Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

“Awesome View” We recently stayed here and it was perfect. The villa was very clean and well maintained. They have everything you need there (beach towels, cooler, chairs, pots, pans, appliances, wifi). There is a/c in both bedrooms and it cools the place off very nice at night. It has a large glass door that opens up to the deck where you have one of the best views of the island. The view is simply breath-taking. Relaxing in the evening on the deck with the view was one of my highlights of the vacation. The property is about 5 minutes from town. Their property management company met us at ferry dock and gave us tour of the town and villa. This is an awesome property and wouldn't hesitate to stay there again. I don't have one complaint about this villa. Highly recommended!

Match: Swimming pool

All filters match

Price per night from

$1,031

Beauty, Comfort, Value! Your Home in the Caribbean

Charlotte Amalie house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Magical Vacation” Thank You Gail & Curlson for allowing us to rent from you. The instant we got to your place, we felt like we were "home". The location of your property is perfect, a short drive to Red Hook and close to some gorgeous beaches. The villa included many "little" amenities such as beach towels, paper goods, hairdryers, that really made my packing job much easier! The kids had the best time swimming in the pool & hot tub and ask daily when we can go back! I think even breakfast tasted better because we were able to eat it every morning on the patio overlooking St. John and Sapphire Beach. Whenever we had a concern or question, you were a quick phone call or email away. And the place looked exactly as it does in your pictures. This was one of the best vacations our family has ever taken. Thank you from the bottom of my heart - Take Care!

Match: Swimming pool

All filters match

Price per night from

$542

'Billion$ View' New Deluxe 2FL Beachfront Villa

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 7

Match: Swimming pool

All filters match

Price per night from

$654

Luxury Honeymoon Suite/ Wifi/ Gated/ Privacy/ Private Pool/ Hot Tub

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Best Place On Earth!!” Where do I begin... My husband and I were on our honeymoon. Dana and Jason were the best hosts-they gave you privacy, but if you need assistance they were always there to help. They made us feel at home in the HarmonySuite with happy smiles and open arms. We were given breakfast every morning-tastes of the Island foods- DELICIOUS ; ) It was amazing to see the iguanas that would come up to the deck to visit. The rooms were well-kept and well-stocked Dana and Jason have everything at your hands. The pictures don't lie the VIEWS were phenomenal-(I think I have a billion pictures of just the view) It was awesome to wake up and come home every day to the spectacular views. The pool/cabana and hot tub were extra touches to this fantastic getaway and are exclusively for your enjoyment . The people on the island are the best so sweet, helpful, and genuine-always great to be around, the beaches are jaw dropping we never wanted to get out- recommending COKI BEACH/ MAGENS BAY and night life was amazing recommending DUFFY'S LOVE SHACK/ SENOR FROGS (RED HOOK) all of this plus much more all located about 6-8 minutes away (car recommended). Can't wait to go back to the best place on earth!! Dana & Jason we love you, Thank You for making our honeymoon a time to remember forever..God Bless

Match: Swimming pool

All filters match

Price per night from

$338

Viewing 38 of 232
rentals in Flag Hill, Saint Thomas

×

Also consider