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Caribbean Holidays & City Breaks - Holiday Lettings
1,517 properties suitable for city breaks and holidays
from £86 / night
£573 - £813 / week

from £40 / night
£275 / week

from £82 / night
£543 / week

Holiday hotel apartment with shared pool in Dominican Republic
Puerto Plata Town hotel apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
from £100 / night
£634 / week
from £46 / night
£273 / week
Holiday apartment in Dominican Republic
Santo Domingo City apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from £40 / night
£275 / week
Holiday penthouse with shared pool in Caribbean
Puerto Plata penthouse
- 2 bedrooms
- 2 bathrooms
- sleeps 6
from £114 / night
£636 / week
from £64 / night
£382 / week
“Sev glorious weeks in a comfortable house, in the pure nature, c” Strongly recommended! In the Mango Stone Cottage I have spent seven wonderful weeks. It is the house that satisfies me as an architect too. It is very well positioned in the surrounding; you are alone, however you feel, that people are not far. The figure of the house is completing the beautiful environment. The concrete structure, stonewalls, open rafters, all made on high level. The interior is a large room and separated bathroom; kitchen is part of the terrace, looking on the river. Large doors opened on the terrace are connecting two spaces and you feel it as your living space. For me comfort ... On the terrace I live: I cook, I eat, read, relax ... from the terrace it is 15 meters into the river, from the same terrace it is about twelve comfortable minutes to the atlantic coast - Bout Sable Beach. And about one minute to the Riverside Café - I love this place with good food, good drink, and good people. I would like to share my best experience. It's authentic text, written directly on the terrace of Mango Stone Cottage, sent from the Riverside Cafe via email to a friend: "I get up at dawn, about half past six. I am not going to the bathroom, flirting with the Taberi River. People are not in sight, so I strip naked, and enters into Taberi River. It is not the hottest, but very OK. It lasts half an hour: adjust the pool on a comfortable lying, and water massages me. After a further slight modification, it works as a countercurrent flow to swim. The head is cleaned from sediments of sleep, the body encouraged. Out from the river, and is clear to me, that one cannot wipe, the goose flesh disappears. With a towel around hips and a banana in hand, I wonder what's next. Come on to take a coffe in the Riverside Cafe, and after to take a bath in warm atlantic waves. But there is a numerous possibilities what to do, I don't know, how to realize it in seven weeks.”
from £132 / night
£772 - £1,089 / week
Villa rental in Trinidad and Tobago with swimming pool
Prospect villa
- 3 bedrooms
- 3 bathrooms
- sleeps 8
“Home away from Home” Amazing experience at Villa Nirvana. The service was impeccable. The owners called frequently to ensure the stay was going well and they are very understanding people. There was a cleaner that came in everyday and all amenities were provided. The villa has all the comforts of a house and an amazing pool which is great for after a long day at the beach. The rooms are spacious and the view from each room of the Buccoo Reef was amazing.We loved the privacy of the place and the lovely peaceful atmosphere. The location is ideal being away from all the hustle and bustle of Bon accord, however is still close to some gorgeous beaches. If there was one thing that could be worked on is the maid service daily I guess depending on the people, and if they would like the service everyday. However, for us with the maid coming everyday it was a bit much. Overall though, the entire experience was amazing and we would recommend and return to Villa Nirvana in a heartbeat!
from £190 / night
£1,177 / week
from £173 / night
£1,087 / week
Villa rental in Saint Mary Parish with swimming pool
Rio Nuevo villa
- 4 bedrooms
- 5 bathrooms
- sleeps 8
from £589 / night
£4,434 / week
“Vida Mejor East Pool and Spa” My family and I stayed three weeks at the East Pool Villa and Spa last august whilst on holiday and had a fantastic time! We have always stayed in Holetown as it has everything you need and we like the area very much. We have previously stayed in studio apartments and hotel apartments which have too been in ideal locations, but even though the latter has been situated right on the beach, we have still felt that there has been something missing. We came across Vida Mejor Villas through their website and were very impressed... the private pool being the main selling point for us and on arrival we were not disappointed... it was fantastic! With the added bonus of the spa too made it extra special. The accommodation was superb... clean, light, airy and spacious, but homely, every need is met with the added peace of mind of the properties being very safe and secure. I cannot recommend these villas highly enough! They are in a fantastic location with all amenities; shops, bank, supermarket, beach and bus stop just a couple of minutes' walk away. We felt rest assured that if we ever needed anything that the owner Carlton would be at hand and help us with anything we needed, as too Peggy, who was also fantastic. Whilst we were on holiday it was my daughters 13th birthday and Carlton had organised for a big, beautiful birthday cake to be delivered on the day!! Which was a wonderful surprise and very thoughtful, and too which made the day that more special. Our highlight would have to be having your own home from home, in particular the computer with 24hr internet access, flat screen television etc. etc. But above all, having your own pool is amazing, and to which makes such a difference to the whole holiday experience. The property is maintained to a high standard and the exterior including pool is set within beautiful surroundings with ample sun loungers and barbeque. This is all within just a stone's throw away from all you would expect from beautiful Barbados!!
from £273 / night
£1,815 - £2,732 / week
“conveniently located.” Great studio close to all the action yet far enough away to relax and get away from it all. Great beach with the wonderful sounds of waves breaking, no air necessary. We loved and felt quite safe walking in the area, around the lagoon and into old San Juan. Bus system modern and only 75cents. Groceries available at Super Max along with great selection of wines. Studio was very well equipped with beach chairs and cooler. Looks exactly as it says. Updated modern and literally hanging right over the beach. Sat for hours looking out and watching all the action on the beach. Great host too! Can't say enough
from £114 / night
£794 / week
“Looking for oceanfront in Condado - you found it!” Incredible view of the ocean from this lovely 1 BR/1 Ba condo in Condado. Fall to sleep to the sound of the ocean, and wake up refreshed and ready to explore Condado Beach in San Juan. Take advantage of great restaurants in San Juan, or cook your own feast in the condo. The owner has thought of everything so you don't have to.
from £114 / night
£794 / week
“Overall terrific package” Best location, on lovely beach w/ perfect water temp. and no pebbles/shells in water. Gorgeous view. Immaculate, well laid-out unit. All kinds of restaurants nearby. East transportation to Old San Juan -a Must See. Consierge very helpful. We shall return!!
from £226 / night
£1,582 / week
from £87 / night
£431 / week
Villa rental in Caribbean with swimming pool, golf nearby
Rose Hall villa
- 6 bedrooms
- 8 bathrooms
- sleeps 12
“A vacation like no other” We were greeted at the airport by Norman, the most professional driver ever, he made our transition smooth and for a group of 12 adults, that is tough! He had thought of everything - including bringing a second van for our luggage! The staff at the villa greeted us at the door with warm smiles and cool towels, they made sure all our luggage was safely delivered to our rooms and then the fun began! We all stopped and stared at the huge view of the Caribbean Sea spread out in front of us, the breeze, the way the rooms are laid out and the villa itself takes total advantage of that view. We quickly changed, and began the most perfect seven days of nothing but relaxing, laughing and eating punctuated by an occasional sightseeing trip. Derek, the butler completely made the trip, he was attentive, but quiet, helpful but never intrusive - he made us feel so special. Ruby, the cook gave us gormet meals three times a day. We discussed our likes and dislikes the first day and she made it all happen. We did not need to go out to dinner and the one night we went to a lovely restaurant in town, we all agreed that we could have stayed home and eaten at Restaurant Ruby for an even better meal. It is tough to please 12 distinct people, but the staff and managment at Serendipity did just that, from organizing the most incredible massage at the villa, to driving us to out of the way Mayfield Falls, they never stopped working. All the rooms were large and private, we never felt on top of one another, we ate meals in different places, by the pool, in the dining room, on the deck, where ever we felt inspired to eat that day, Derek made it happen. I do not have one bad thing to say - I loved every minute, and would recommend Serendipity to a group like us, a large family, or just a few people that want to get away - It was truly a vacation to remember.
from £654 / night
£5,717 - £12,705 / week
“Totally awesome” I stayed at this Condo in Fajardo, PR with my 86 year old mother, brother and his wife. My brother and I took my mom on vacation to her native Island. So, to say the least we were a bit concern on how she would acclimate and if the condo would accommodate her needs. We were totally beyond pleased with the condo's cleanliness, accessibility for her disabled needs such as wide doors, location on the 1st floor with a ramp. It was so easy for her to get around, I was impressed. The location of this condo is so ideal, I was jealous that it wasn't mine. It is located near the most beautiful beaches in PR, a skip & a hop to the Ferry and very safe with security guards at entry point of the condos. The pools were wonderful, geared towards families with children as well, as singles and couples. The fitness center was well kept and safe. I truly can't say enough about this condo. I highly recommend it and I will be staying at this location on my next vacation. It's idea for couples, family and anyone. And, of course my mom's wish was fulfill, she was very happy that she got to go to PR. Oh, I might add that there are 2 medical centers about 7-8 minutes up the street. That even made us more at ease knowing that if mom needed anything it was so close. I like to end with I wish it were mine... however, I Thank the owner for being so generous and sharing his vacation home! I rate it Outstanding!!
from £114 / night
£794 / week
“Gracious Host Came With Toast” The Villa Vida Mejor Villa was the perfect place for our family to stay on our first trip to Barbados. The moment we arrived (late at night) Carlton greeted us with bread, for toast, tea, and other fixings for breakfast. He was always present when needed, but never intrusive. The Villa is comfortable and spacious, and the private pool is a serene getaway surrounded by tropical plants. It is located in a quiet neighborhood, but only a quarter mile or so from Holetown proper and the bustle of the platinum coast. The kids loved the high speed internet, while we enjoyed breakfast on the terrace. The beach is an easy 10 minute walk away. When we come back to Barbados, there is no doubt whatsoever that we will return to the Vida Mejor.
from £273 / night
£1,815 - £2,732 / week
“Very good location” Carlton was very easy to talk to and ask for help on anything to do with the island. He did all this even before I met him for the first time. So this was setting me up as too how it was to be in person and he was just as pleasant and helpful when we arrived. The house is in a great location and an easy walk to everything you need. We did not see monkeys in the garden but they were on the street in front of the house a few times which was a thrill for us. You will feel very safe in the area where the rental is located as well. The only thing I would have to say that was not up to my liking were the beds. They were really hard and needed a pad on the top of them for more comfort . After being there a week you really felt your back getting sore. One other thing that could have been better was the house keeping. The lady was so sweet and nice to be around I did not dare ask her to do a better job on the floors. It was so minor and we were only there a week so I chose to over look it. I would not even consider staying at another place if I ever get the chance to return. Carlton has my business and I have told others to rent as well from this same place. Well worth the look. Thank You Carlton for the chance to stay at your rental.
from £273 / night
£1,815 - £2,732 / week
from £250 / night
£1,572 / week
“Sweet vacation place!” This was a wonderful, relaxing and secure place to stay. We liked it very much! We would rent again and usually we don't say that! It is as nice or better then the pictures. The place was very clean and kept up and the manager( a Dominican named Isidro) is sweet, watchful and immediately helpful. He met us there within 5 min. when we got there or would call with a question or prob. He even hooked us up with a friend who has a car rental place nearby. Recommendations are everything when you are in a foreign country! Allen the owner spent time explaining everything before we went and had recommendations too! He has been great to deal with! The home is very spacious and the master BR and one downstairs have a direct view of the ocean and the sound of ocean lapping up on the shore made sleeping a dream!!! Loved that feature alot! Being outdoors was wonderful, the backyard is well kempt and the foliage is lovely!! It is so close to the ocean! It is so relaxing and beautiful! The one and only downside is that the beach was not clean along that area. It is a bit of a cove and lots of seaweed comes up, and Dominicans had left quite abit of trash scattered. But there is a clean beach right around the corner where you can snorkel and swim; about 200 yards away. You cannot see it from the yard because of the foliage and small retaining wall. the area is safe and people are very friendly and nice.It is a real look at the DR life with the comforts of american life!
from £182 / night
£1,180 - £1,942 / week
from £63 / night
£439 / week
from £41 / night
£273 / week
from £90 / night
£629 / week
“Perfect Vacation Home!” Very beautiful, spacious condo close to everything! Loved that it is in a gated community. The pool area was beautiful and always clean. I would highly recommend this property and will be back soon!
from £214 / night
£1,493 / week
“Haven Del Mar is Heaven!” Haven Del Mar is a beautiful home away from home in Freeport, Bahamas. I thoroughly enjoyed my stay with my family and will definitely be back. The owners provided excellent accommodations! Whether sitting out back on the beautiful patio under the twinkling stars enjoying soft music, a glass of wine or hanging inside with your family for a game of pool, this is the place to be! The amenities are top notch and access to the island whether by boat or car are ideally located. The home is clean and the decor is beautiful. I recommend going to the Fish Fry on Wednesday nights and the Pepper Pot for a late night snack on Thursday nights! Also, you have to visit the pool at the Ritz Beach Resort as the swim up bar and the secluded jacuzzi's are great fun! ;) Illeana is the Property Manager and is a lovely lady that will provide you with anything that you need. Her Customer Service is superior! Mr. Bucher is kind and helpful and made sure my family had everything we needed to enjoy our stay!
from £226 / night
£1,659 / week
“Not bad but not exactly what we expected..” Donald and the staff were nice and willing to go out of their way to help but he was also definitely trying to make a buck too. I booked a spot for $35 and then he should us a $10 upgrade in which we took. It can be a little bit of a pain with how many keys and locks you have to deal with, personally i liked it but maybe thats because my moms a prison guard. I asked him if it was loud being facing the street and he said no its real quiet. It was really loud. Luckily I can sleep through anything so I wasn't that bothered. Then we prebooked the same place (had no time to shop around), prepaid for it only to come late at night and he had put us in another spot that wasn't as nice and didn't have the separate kitchen area. I had to mention it to him to give us $10 back. He offered us a ride to our bus for $15. You can get taxis much cheaper. Summary, the place is comfy with a comfortable bed, can be loud and not the best neighborhood. Donald is nice but he is trying to make money too. Its a good price but if you search well you can find that price or better right in the Colonial Zone. Wasn't horrible but I won't be back.
from £19 / night
£127 / week
“Great Place to Stay, better than hotels” My family and I stayed in this lovely villa for two weeks (Myself, Wife, daughter, Son). My mom also came for the 2nd week. The driving directions were spot on and we were promptly greeted by the house manager who had the key and give us a quick tour etc. The home is lovely and looks just like it does in the pictures, 3 bedrooms, nice outside deck with a pool and BBQ. The home is modern, up to date, clean, and well cared for. The property manager lives close by and he was not intrusive, but available if needed. We did not need anything in the villa, but since he lives next door is was nice to say Hello when we saw him. It was like having a friendly neighbor that you knew. The neighborhood was quiet and safe. We were able to save money by cooking a quick breakfast every day, then packing lunch (utilizing the owner supplied coolers) before heading off to the beach. Sometimes we had dinner out; sometime we had a nice dinner in the villa (American style BBQ). AC was cold, kitchen had all that you would need, two bathrooms, two showers were extra nice so we could get ready to go out quicker etc. You can walk up to the Sulton restaurant. I loved having 3 bedrooms, I like to go to bed early and wake up early. This way the kids could stay up a little longer and not wake me up (can’t do that in a hotel!). Plus, everyone can have their privacy at night. I would recommend this property to anyone. Keep in mind this is someone’s home, we cleaned up after ourselves. If we stayed at a hotel, our trip would have been shorter. Flipkey, Airbnb etc allows you to save money on your stay and affords you the luxury to cook and save even more. Thank you for a great Stay Alexander!
from £128 / night
£835 / week
“best stay ever !!!” This rental has everything that you need to make you stay the best ever. I was expecting the apartment to a little different from the pictures but every thing is exactly what is in the pictures. Andy made my stay very welcome if I needed anything thing I could have give him a call or the manager a call and it was done by time I got back from my day out. There was a welcome dinner as well and some breakfast items when we arrived. The wifi was excellent we has service though out the apartment no dropped signal. The rooms were very comfortable. I loved the balcony the most. Just to waking up and opening the doors and having that beautiful view of the ocean...boy was I in heaven. The only thing that was a bother the need for transportation. But if you like to walk and experience Barbados then that would not be a problem just down the hill to the bus in to the city. But all in a nutshell it was by best stay ever !!! Never going any where else.. This marks my spot for all my vacations to Barbados
from £78 / night
£547 / week
Holiday apartment with shared pool in Caribbean
Montego Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
“In one word awesome!” My husband and I recently stayed at the Seacastle Getaway Beach Penthouse. We had the time of our lives.If you want a peace of mind and tranquility this is the place to be at not to mention the room "fabulous". My husband and I didn't want leave but unfortunately we have to. Right now we're planning another vacation and definitely its will be Seacastles Getaway Beach Penthouse.
from £154 / night
£1,074 / week
Holiday apartment with shared pool in Caribbean
Santo Domingo apartment
- 1 bedroom
- 2 bathrooms
- sleeps 2
from £55 / night
£382 / week
from £55 / night
£409 - £1,044 / week
“Excellent convenience and comfort!” Stayed in the apartment for approximately 10 days and it was an ideal accommodation to experience Santo Domingo and nearby beaches away from the tourist bubbles and in a superb residential area. Right from the start, Francisco and Gisselle were always very quick to respond and great to interact with. Francisco contacted me to confirm my arrival the day before and with one phone call once in Santo Domingo, the taxi from the airport found the apartment with no problem. Giselle was already at the apartment and the whole check-in process was extremely friendly and quick. The apartment itself has all the essential amenities and even comes with a blender which came in handy and towels for both the bathroom in the main bedroom as well as the guest bathroom, etc. All of the furniture and household items are kept in good condition and the stools by the kitchen are a very nice touch of elegance. I was even provided with an additional cooking pan with no troubles. Jose, the concierge in the building during the day, was always very helpful and friendly and often helped me with last-minute directions. The building itself is quiet, as are the neighboring residences, which makes for a very restful stay. Cleaning is also provided once a week at no extra charge. What I most valued was its superb location as a liquor store (Drinks to Go), a large supermarket, and numerous restaurants and similar venues are all within walking distance to the apartment. Also, finding my way back to the apartment by taxi from different spots in the city was relatively smooth and trouble-free even for a first-time visitor like me. I would have welcomed an apartment on a higher floor with a panoramic view or a bath tub in the main bathroom, but these are very minor aspects that hardly take away from the overall luxury of the apartment. Indeed, I highly recommend this apartment for the business traveler or those on vacation who are after a mix of ideal location and completely comfortable atmosphere.
from £68 / night
£454 / week
from £87 / night
£604 / week
“We just loved everything about it!” We decided to take in some city culture for our last 3 nights in Jamaica. I am so glad we decided to stay at Signature's 21 in Long Mountain. The setting is fantastic and the photos on line don't do the views or the condo any justice! The area is super exclusive and secure. After a day in the heat and chaos of Kingston, it was a relief to come back 'home' at the end of the day. All the comforts of a north american home are there (really good bed, full kitchen, washing machine, hot shower with good water pressure, A/C, etc.) and the place is very clean. We enjoyed and appreciated the private and serene outdoor area which is nicely planted with bougainvilleas, fruit trees and a beautiful big palm tree in the middle. We spent so much time relaxing on the perfect patio (which is also nice and shaded), it was hard to want to leave to explore the city! The location is great, especially if you're driving. Within a few minutes drive you can find the best blues bar (Red Bones), the best ice cream (Devon House) and even the best Indian food (Tamarind Indian Cuisine). You could really spend your whole time in Kingston visiting places just a few minutes away! At the same time a drive downtown is less than half an hour and certainly worth seeing. The National Gallery is fabulous (and free on the last Sunday of every month). If you are in Kingston on a Saturday, go explore the bustling 'ben dung' market right in the centre of Downtown (Parade area). Kingston is a city of huge contrasts and I couldn't help but feel a bit bourgeoise returning to the luxury of Long Mountain. However a vacation is supposed to be a relaxing escape and I sincerely cannot think of anywhere else in Kingston that offers the peace and beauty of Signature's 21.
from £81 / night
£409 - £536 / week
“Great Place To Stay” These was our first trip to Vieques and we decided to book and stay in andrea's House and had a blast. The house is very comfortable. We were very pleased with what we found there. Very clean, fresh and beautiful place. Absolutely we will stay there again!
from £114 / night
£544 - £1,497 / week
“Balling on a budget” My 7 friends and I from UWI made this our home for the mini vacation we spent in Ochi Rios. The location is great, situated about 5 mins from the town and walking distance to Margaritaville! The house is fully equipped, with 2 showers and 3 toilets, 1 kitchen containing utensils, 2 bedrooms containing both fans and air conditioning, wifi and cable tv. The compound is clean and noise free. It has multiple pools available for use at anytime. Best of all it was affordable on a student budget!
from £90 / night
£629 / week
from £68 / night
£459 / week