Flag Hill, Saint Thomas Rentals with Pools

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408 rentals in Flag Hill, Saint Thomas with pools

Great rentals within 20 miles that match your search

Sapphire Beach Front (Fully Renovated)

East End condo

1 bedroom / 1 bathroom / sleeps 4

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$309

2 & 3 Bedroom at the Ritz Carlton - All Dates Available, Even Last Minute!!

St. Thomas hotel apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Paradise!” I highly recommend The Ritz in St. Thomas. It has absolutely everything you need to have the vacation of a lifetime. Whether you're going with your kids or just as a romantic getaway...there is something for everyone. This unit is gorgeous! The renter is super easy and very nice to deal with. Highly recommended!!! Would definitely vacation there again.

Responds fast! avg. 2 hours 16 minutes

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$721

SAPPHIRE VILLAGE EAST END ST. THOMAS Fall Sale!!

Charlotte Amalie apartment

1 bedroom / 1 bathroom / sleeps 2

“Honeymoon stay” The room was awesome!! The view was spectacular! Super clean and cozy. The bed was perfect. We will definitely be back next yr. Also the pool and the Sapphire bar and grill is only steps away from the room. Of we could've stayed longer, we would've.

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$228

EXTREMELY HIGH REVIEWS! Owner lives in Community to Help, if Needed. Sleeps 6.

East End apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Outstanding Condo, Location, and Amenities” The condo was spacious with excellent appliances, furnishings, and amenities. Sherry was a fantastic host; she provided all the information we needed to enjoy our 2 week stay at Cowpet Bay West. The adjacent pool and beach were excellent. The on-site restaurants were convenient and provided great meals. We will definitely return to this condo for our next stay on St. Thomas.

Responds fast! avg. 2 hours 24 minutes

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$343

St. John, USVI, Blue Agave Villa, 4 bedroom, dazzling sea view, pool, Cruz Bay

Cruz Bay villa

4 bedrooms / 4 bathrooms / sleeps 9

“Awesome View” We spent a week at the Blue Agave with 3 other couples. The set up was perfect as each couple had their own private bedroom and bath. When choosing a house for our vacation our main concerns was having master suites for all couples. Three of the suites had king beds and the fourth bedroom had a queen. That was all perfect. The other main concern was having a home that had a covered deck so we all would not crisp. Well this house was excellent for shade. There was a beautiful spacious deck with pool and lots of covered space so that no one had to sit in the sun unless they wanted to be. There were two tables under the shade area so plenty of room to eat any meals outside while enjoying the beautiful view. Always a nice cool breeze outside under the covered veranda area. We enjoyed watching the sugar birds come and go. Very entertaining. We put sugar on a plastic plate and set it on a post and had constant entertainment from the sugar birds. We would enjoy renting this home again if we should ever get back to St. John.

Responds fast! avg. 2 hours 11 minutes

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Price per night from

$591

Blackbeard's Hideaway Tortola BritishVirginIslands

Road Town house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 52 minutes

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$1,048

WOW Views! Stays Assist U.S. Military! 2BR/2BA Caribbean Escape-St.Thomas USVI

East End apartment

2 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 42 minutes

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$274

Villa Mirino, Ocean front, Intimate East End Home

East End villa

5 bedrooms / 5 bathrooms / sleeps 10

“Beyond Expectations” I would not stay anywhere else on the island. The house itself is in immaculate condition with huge sliding glass doors in every room allowing for amazing views of the Caribbean from every room. I loved waking up to the breathtaking sunrise every morning and the house's beautiful décor encourages complete relaxation. Whether watching TV, playing Xbox/Playstation or listening to music via the surround sound system, it felt like our every whim was met. The kitchen is stocked with gourmet appliances and cookware which made my ability to create fantastic meals for us easy and fun. When we tired of laying by the pool, the beach was less than a mile away and the Red Hook night life was right down the street. This villa is truly one of the premier locations on the island. I cannot wait for the next trip back

Responds fast! avg. 2 hours 20 minutes

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Price per night from

$688

Condo on Beach Caribbean/Pool 40'Out Rear

East End apartment

1 bedroom / 1 bathroom / sleeps 4

“Amazing place with views!” My husband and I had a great time in the condo. The location was fantastic, and we thought the condo was in amazing shape. I loved all the kitchen - very nice and easy to throw together light dinners. We would definitely stay here again and recommend to friends!

Responds fast! avg. 3 hours 24 minutes

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$195

2 Bdr Condo on the water in the beautiful Caribbean

Bolongo Bay condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 2 minutes

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$298

Beauty, Comfort, Quality, Service... Your Island Home in the Caribbean!!

East End house

2 bedrooms / 2 bathrooms / sleeps 6

“Can't wait to go back!” Of the several places I've staying on St. Thomas (and St. Croix) the past year, this is the best. I loved all the thoughtful touches: comfy, LONG chaises; lovely pool; beautiful balcony; fantastic, well-appointed kitchen and bath; extra towels, linens, and bathrobes! Everything was spotless. The pool was kept clean. The winds keep the mosquitoes away. Completely quiet but restaurants, supermarket, etc. all easy to get to. Very caring owners and the whole experience was professional but very kind. Loved it!

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$241

20% Discount for dates in December - Inquire Today!

Cruz Bay villa

4 bedrooms / 4 bathrooms / sleeps 8

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$665

Caneel Trailside Cottage: Expansive Views of the Caribbean!

Cruz Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

“Every thing was neat and tidy and just right for us.” Our first visit to this villa and we loved it. Two equal sized bedrooms and everything you could ask for. Great view and close to town. We will rent here again. Catered to was great to work with and gave us super service.

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Price per night from

$430

Point Pleasant - USVI - Villa East - Best Location

East End studio

Studio / 1 bathroom / sleeps 4

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$114

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.

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$172

Oceanfront St. Thomas Villa w/Pool,Spa&Bay Views!

Peterborg villa

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 26 minutes

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$459

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!

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$574

Sapphire Jewel

East End condo

1 bedroom / 1 bathroom / sleeps 4

“Super comfortable condo, excellent value, owners thought of everything” We stayed at this Sapphire Bay condo this February for a week and it was paradise. It is on THE best beach in the Virgin Islands. Everything about the condo is perfect including the bed, which was so comfortable we wish we had it at home. The owners have provided all the comforts of home. The kitchen is so we'll appointed we were able to cook gourmet meals and have friends over and have dinner parties at the elegant no generous sized dining table. The a ir conditioning worked well. The View from condo was absolutely gorgeous. The location was the best- Close to stores, beach, marina... Everything! This is a great vale (I hope owners don't raise rates reading this because we want to come back next year, but the price makes it an incredible value) 10 stars for this rental

Responds fast! avg. 3 hours 7 minutes

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Price per night from

$201

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

Responds fast! avg. 2 hours 21 minutes

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Price per night from

$316

Villa in Paradise w/Private Pool! Walk to beach!

East End villa

1 bedroom / 1 bathroom / sleeps 4

“Perfect vacation in St Thomas” Spent end of January, beginning of February at Laverne's place in Pavilions and Pools. Everything was perfect. The condo was clean and very comfortable. It was great having your own pool just outside the door. The property was quiet and peaceful and We really enjoyed our stay here. The girls at the front desk, the maintenance people, everyone at the facility were extremely friendly and very responsive to any of our requests. Vicars, the on site restaurant was excellent. If you go there, order the steamed mussels appetizer. It was fabulous. Every morning there are bagels, muffins, cereal, juice and coffee if you don't feel like making your own breakfast. We also used the grill to cook a few steaks during our stay. The only slight drawback was the walk to the beach, it was approximately 5 minutes long, but seemed worse if you are carrying beach chairs, towels, etc. However, once you get to the beach the walk was worth it. Sapphire Beach is a really nice beach, with changing and rest room facilities and a vendor (Banana Bar) that serves sandwiches, drinks etc. From the beach it's a short walk to the Marina where you can see the Tarpon & Barracudas swimming in the clear waters. Red hook was a great area for restaurants or a trip to St Johns and it's only a few minutes away. We did not have a car and didn't need one. The Safari taxis stop right in front of the hotel, and regular taxis are not that expensive and easy to find. Don't miss the fiddle player at Latitude 18 on the other side of the Red Hook Harbor.

Responds fast! avg. 3 hours 11 minutes

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$253

Cruz Bay Luxury Studio Apt.~ A+ View

Cruz Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 0 minutes

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$256

Pool-Private Snorkeling Beach-Free Kayaks

Virgin Islands National Park villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 11 minutes

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Price per night from

$396

Cabrite Paradise Oceanfront Elegant Villa, Pool, Private, stunning views !

East End villa

2 bedrooms / 2 bathrooms / sleeps 5

“Awesssooommmeee” Was reluctant to write this review, because didn't want other people renting possible time, I might rent again. It was the most relaxing time,I have ever had in ST.Thomas, the view was breathtaking,as much as I love ST.Thomas,i never wanted to leave Cabrite point,was never in a hurry to do anything or go anywhere , perfect place to experience, what they refer to has island time.I would highly recommend this to anyone looking to get away from the daily grind, lay back and relax and enjoy the view as well as the trade winds ,you won't regret it, my only regret was that we had to leave after 3 weeks , next time will book it for a month

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$246

Casa Azul at Crystal Cove, St. Thomas

Red Hook condo

1 bedroom / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 38 minutes

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$343

Studio Condo on the Waterfront at Bolongo Bay

Bolongo Bay condo

/ 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 2 minutes

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$184

SAPPHIRE DESIRE *Amazing views!!* Oceanfront Condo St. Thomas, VI

East End apartment

/ 1 bathroom / sleeps 2

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$148

Magens Bay, Pool, Amazing View, New Construction, Exquisite Comfort, Gated

Magens Bay villa

4 bedrooms / 5 bathrooms / sleeps 14

“Beautiful well-equipped home, very relaxing, lots of privacy, st” My husband and I rented Blue Skies for a week's stay with our two college-aged sons during their Spring Break. We were looking for a family bonding week, and this definitely fit the bill! Blue Skies Magen's Bay offered an exotic, gorgeous setting that made their jaws drop! Not your ordinary "been there/done that" vacation. This location makes memories. At Blue Skies, both sons had their own quarters, which they loved. They slept in to their hearts' content while we sipped coffee on the covered porch and watched the iguanas sunning. Everyone enjoyed time reading, laughing, playing cards and trying to navigate around St. Thomas. The grocery service was great, the 2 helpers on the island and Shawna, the homeowner, are extremely helpful. We did get a few more groceries one day, even. We did one outing to Magen's Bay Beach -- just lovely. And another day on St John, snorkeling at Trunk Bay and driving around. Ate dinner out 3 times, quite the adventure. The home is incredibly well-furnished. All the beach/picnic supplies you could want, kitchen utensils galore, good knives, blenders, coffeemakers -- people generously left olive oil, cooking spray, spices, condiments and more. A positive vibe where people had taken care of the place and respected its beauty. The deck has plenty of shade and plenty of sun, the pool is just right for cooling off. The view will leave you breathless! I would recommend this property to friends and family. It was clean and matched the photos and description perfectly.

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$476

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.

Responds fast! avg. 30 minutes

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Price per night from

$591

Villa stomach

Magens Bay villa

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$607

Edge of Paradise Villa- The Ultimate Getaway

St. Thomas villa

4 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$1,556

Chateau Margot

St. John villa

6 bedrooms / 6 bathrooms / sleeps 14

“Wonderful” Chateau Margot was perfect for a family celebration and holiday. The three seperate buildings gave privacy and comfort for the three different families on this trip. The terrace was perfect to enjoy the spectacular views and get together for breakfast and afternoon cocktails. The house is very well appointed, tastefully furnished and very quiet.

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Price per night from

$858

Mango Manor Guest House

Road Town guest house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$574

Westin St. John Luxury -- Three-Bedroom Pool Villa

Cruz Bay villa

3 bedrooms / 3 bathrooms / sleeps 8

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$1,147

Top 10 Reasons to Stay at Our Place in Sapphire

East End apartment

1 bedroom / 1 bathroom / sleeps 4

“Home away From Home” This condo was the perfect choice for our stay in St. Thomas. It was close to everything; the beach, shopping and recreation, yet it was quiet and private. The place worked well with our family of four. There was a private bedroom and two full size futons in the living room for the kids. The pool was not crowded with the Sapphire Grill a bonus we didn't expect. We ended up having lunch by the pool a few times. The snorkeling at Sapphire Beach was outstanding. We will definitely stay here again.

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Price per night from

$201

La Bella Vita: Sunset Views Year Round!

St. John villa

4 bedrooms / 5 bathrooms / sleeps 8

“Extraordinary home with ever changing views” Our group of six has been traveling to Usvi for 6 years. We have worked with Catered To for four of those years and they are the best. In the planning stages for this trip my conversations with Catered To were very helpful. They weren't just interested in renting any property, they wanted us to have the best possible experience. This is our first stay at La Bella Vita and we give it an a+ rating. The views were magnificent especially in the mornings when the sun was coming up and in the evenings during sundown. The colors and the views were constantly changing. They can't be described. The villa was very comfortable and stocked with all the amenities that we needed. We would have liked to see more lounge chairs around the pool and more comfortable outdoor furniture but overall it is on our list as a return property.

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$859

Waterfront Escape: Paradise at a Great Price!

East End studio

Studio / 1 bathroom / sleeps 4

“Perfect Honeymoon” My husband and I stayed at this property at the end of June/early July for our honeymoon...which ended up being great because St. John was celebrating carnival! We didn't rent a car and had no trouble navigating the island. However, we like to do things "off the beaten path"...I don't think everyone would enjoy the safari buses or "gypsy" taxi drivers, but we really enjoyed both and you can't beat the price. $1 per person go travel to Red Hook?! Billy's list of transportation, activities, etc. was amazing. We went to Coki Beach - interact with locals and snorkeling, St. John - hiking/beautiful beaches/carnival, Red Hook for groceries and restaurants/bars, Charlotte Amalie for shopping/pier/more food (avoid at all costs on Tuesdays and Wednesdays - cruise ships come in these days), Magen's Bay - beautiful and great to relax, Linquist Beach - this one was a little to windy and too much sea grass for me, but my husband enjoyed it. Some of our favorite restaurants were Duffy's (not so much the food, but the atmosphere and bartender were great), XO Bistro (amazing food and cocktails, fine dining atmosphere), Greengos (Mexican cuisine in Charlotte Amalie - fun sitting in the shopping corridors), Tap & Still (great burgers). Latitude 18 was our absolute favorite. Laid back, live music, great food, and friendly locals right on the water. The actual condo was perfect for us because we were out and about except to shower and sleep. I did cook breakfast almost every morning (there was plenty of cooking equipment for this), but we ate at a different beach or restaurant for every other meal. There were plenty of towels (for showers and the beach), bedding, and toiletries. We loved the coolers, so we could save on beverage costs when we went to the beaches. The only confusing part was the transportation around the resort. Initially, we were told we had to pay $40 a day for transportation. We kept calling for golf cart rides to the front gate (where we would catch the safari bus or a taxi)...waiting for them to ask us for payment, but they never did. A couple days into the trip, I met a very friendly resort employee and she said that was absolutely incorrect and the resort employees will take us anywhere on the grounds for no charge. The $40 a day transportation is if you wanted to go anywhere off grounds. Not a big deal, but incase someone else is told they have to pay $40...here you go. Billy was great to work with and his communication couldn't have been better. All-in-all, we can't wait to come back! It was an amazing start to our marriage :)

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Price per night from

$270

Mooncottage: Most Romantic St. John Petite Luxury Villa in peaceful Coral Bay

Coral Bay villa

2 bedrooms / 4 bathrooms / sleeps 4

“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!

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Price per night from

$655

Studio Condo on Bolongo Bay

Bolongo Bay condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 2 minutes

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Price per night from

$172

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