50 Best Caribbean Villas on Holiday Lettings - Vacation rentals

Close

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

21,963 Vacation rentals

(35) Excellent 

17

Vacation townhouse with swimming pool, golf nearby in Caribbean

Saint James Parish / Holetown

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
With interior spaces inspired by New York lofts,12 ft high ceilings, huge rooms, and plenty of natural light, Hillside Villas at Limegrove is a unique Caribbean environment. With over 3,400 sq feet of internal space, over three floors, with three double bedrooms and bat …see more

from $355 / night

$2,481 - $5,981 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from $355 / night

(3) Good 

23

Vacation villa in Guadeloupe

Grande-Terre Island / Sainte-Anne

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
Very close to the beach Bois Jolan, this duplex villa offers 5 beds spread over 3 air conditioned bedrooms, 1 bathroom, 1sde, 2 WC, 1 open living dining on American cuisine. Enjoy the quiet surroundings to relax on the terrace between visits to our beautiful island. The …see more

from $74 / night

$513 - $558 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from $74 / night

(23) Very Good 

35

Vacation apartment with swimming pool in Caribbean

Saint Peter Parish / Mullins

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Supernova, located at the north end of Mullins Bay. A spacious ground floor apartment offering 2 good size King/Superking bedrooms. With Indonesian furnishings, this apartment oozes quality and style. Marble floors throughout. Black granite surfaces. Picklepine wardrobe …see more

from $255 / night

$1,783 / week

Book View

from $255 / night

(5) Very Good 

12

Vacation apartment in Caribbean

Holetown / Lascelles

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Sunset Blue is a luxury family apartment in tropical gardens with huge private outdoor pool and patio area. All renters have exclusive use of the pool and gardens. Accommodation is for 4 people in 2 bedrooms /2 bathrooms. A double sofa bed is also available for 2 extra …see more

from $153 / night

$1,019 - $1,732 / week

Book View

from $153 / night

(6) Excellent 

30

Villa rental in Caribbean with swimming pool

Turks and Caicos Islands / Providenciales

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
REEF TIDES IS YOUR ULTIMATE LUXURY CARIBBEAN FAMILY VACATION VILLA WITH SUPERB VIEWS, LARGE TROPICAL GARDENS AND SNORKELLING REEF Walk through the front entrance of Reef Tides and you are greeted by a breath-taking view straight from a tropical fantasy. The vivid blues …see more

from $1,350 / night

$9,450 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from $1,350 / night

4

Apartment rental in Caribbean with shared pool

Curacao / Willemstad

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
The accommodation is well located near shopping center with mini-markets within walking distance, close to the airport without noise and located along the ring to the center of Willemstad. Equipped with a swimming pool with sun loungers. How can you enjoy under the pala …see more

from $46 / night

$319 / week

Book View

from $46 / night

(52) Excellent 

15

Vacation villa with swimming pool in Barbados

Saint James Parish / Holetown

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.7 mi
  • Swimming pool
Beija Flor villa is a beautiful 3 bedroom luxury house with private pool and covered terrace for alfresco dining. It is situated on the outskirts of Holetown, in the popular parish of St. James. It is 10 minutes walk to Heron Bay beach with white sand surrounded by the …see more

from $269 / night

$1,881 / week

Inquire View

from $269 / night

(6) Very Good 

34

Bahamas Vacation home rental

Great Abaco Island / Marsh Harbour

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Child friendly
Our House is located 16 miles southwest of Marsh Harbour ,Abaco,Bahamas. House is a duplex with 2 similar appartments , in each appartment there is 1 bedroom with queen size bed , 1 kitchen , 1 bath , 1 shower, 1 mainroom with convertible futon and rattan furnitures . …see more

from $200 / night

$1,400 / week

Book View

Responds fast!
avg. 2 hours 26 minutes

from $200 / night

(1) Very Good 

39

Vacation guest house in Caribbean

Hanover Parish / Lucea

3 12 1 night min

  • 3 bedrooms
  • sleeps 12
  • 1 night min
  • Nearest beach 24 mi
  • Child friendly
  • Air conditioning
This high-spec holiday home has a unique location in rural Jamaica with breath-taking views, stunning wildlife, forest, mountains and a chance to experience the real Jamaica. It is in the undiscovered village of Bessie Baker - a 45 minute drive from Montego Bay airport …see more

from $35 / night

$240 / week

Book View

Responds fast!
avg. 18 minutes

from $35 / night

(27) Very Good 

33

Home rental in Caribbean with swimming pool

Saint Peter Parish / Maynards

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Palm Villa is the perfect holiday home in Barbados. Its elevated position at Maynards allows the easterly tropical breeze to gently cool you down on the hottest of days. The house has been fully refurbished in 2011 with modern furniture and all the modern conveniences y …see more

from $249 / night

$1,738 - $3,253 / week

Book View

from $249 / night

10

Vacation home with shared pool in Guadeloupe

Basse-Terre Island / Sainte Rose

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Top comfortable villa close to beaches and golf Corner calm hiking, swimming and deck.A 5mn shops (Super U, doctors, restaurants ...). Hikes Large Marine cul de sac are 10 minutes by car, the sulphurous baths of Sofia. 10 minutes of Deshaies beaches. You'll be close to …see more

from $80 / night

$559 / week

Book View

from $80 / night

(13) Excellent 

23

Vacation villa with swimming pool in Caribbean

Saint James Parish / Weston

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to our piece of paradise on the west coast of Barbados, just north of Holetown. Westshore Beach House has been fully renovated in a contemporary style to provide a secluded hideaway, situated on the beach. A beautiful beachfront house with spectacular ocean vie …see more

from $950 / night

$6,650 / week

Inquire View

from $950 / night

21

Caribbean Vacation home rental

Cabrera / Orchid Bay Estates

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
WONDERFUL VILLA WITH MAGNIFICENT VIEW ON THE NORTH COAST D ELA HIGH RANGE DOMINICAN REPUBLIC ANY COMFORT FRENCH HOT SOLAR ELECTRICITY AT 8 KM FROM THE SEA ON 2500 M2 OF LAND WITH PLANTATIONS OF BANANA ORANGE TREES AVOCADO ETC... SWIMMING POOL WITH ITS JACUZZI BBQ AT DIS …see more

from $91 / night

$626 - $638 / week

Book View

from $91 / night

11

Caribbean Vacation apartment accommodation

Arrondissement of Le Marin / Le Vauclin

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Air conditioning
rent a beautiful villa top F3 newly renovated quiet in height vauclin, the beach road, and the best kite spots, with beautiful countryside views, air conditioning, wifi. the equipment of this apartment will allow you to only arrive with your suitcases contact us !!! …see more

from $69 / night

$342 / week

Book View

from $69 / night

(25) Excellent 

24

Vacation hotel apartment with shared pool in St. Lucia

Castries Quarter / Marigot Bay

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Our 2 bedroom, 2 bathroom luxury apartment comes with spectacular views across the resort, marina, bay and tropical hillside. It has a fully equipped kitchen, lounge and utility room with all the conveniences you would expect from a modern apartment; floor to ceiling wi …see more

from $273 / night

$1,899 - $3,291 / week

Inquire View

from $273 / night

(16) Very Good 

26

Vacation home in Caribbean

Bottom Bay / Apple Hall

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Whistling Frog - Absolutely Stunning describes this newly constructed house with its ocean views, swimming pool and landscaped garden. It’s just 200 yards from Bottom Bay Beach – and a short walk to numerous deserted bays/beaches in close proximity including, Foul Bay, …see more

from $89 / night

$633 - $722 / week

Book View

Responds fast!
avg. 3 hours 57 minutes

from $89 / night

19

Caribbean Vacation b&b rental

Basse-Terre Island / Saint-Claude

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Nearest beach 15 mi
  • Private garden
Pretty bedroom with bathroom in nice wooden villa U. Seaview calm without opposite !! You will have the kitchen .so that the stay and parking on site ... At the foot of the volcano La Soufrière you can enjoy many walks in tropical forest ..and various rivers. The calm o …see more

from $69 / night

$479 / week

Book View

from $69 / night

(43) Excellent 

19

Vacation bungalow rental

Basse-Terre Island / Sainte Rose

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Air conditioning
Change of scenery, peace and comfort is what you will find at Coco Bungalows. Bright colors, air-conditioned bungalows, located between St. Rose and Deshaies, 100 m from the Caribbean Sea. Coco Bungalows is located in the center of Guadeloupe, ideally located for the de …see more

from $68 / night

$470 - $582 / week

Book View

from $68 / night

(1) Excellent 

43

Vacation condo rental

Curacao / Willemstad

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The Strand Sun Ray is a 3 bedroom luxurious condominium on the third floor. From the balcony you have a breathtaking view of the crystal clear lagoon with sandy beach and the Caribbean Sea. The private sandy beach features nice palm trees, palapas (umbrellas) and lounge …see more

from $211 / night

$1,474 / week

Book View

from $211 / night

87

Vacation apartment in Caribbean

Bequia / Richmond

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 0.75 mi
  • Swimming pool
  • Car not necessary
Tropical Hideaway is a luxurious and very private property, consisting of five boutique accommodations surrounded by vibrant and mature tropical gardens. Set in over 4 acres of pristine natural forest all accommodations offer private facilities to the highest of standar …see more

from $410 / night

$2,611 - $4,165 / week

Book View

from $410 / night

(11) Very Good 

Certificate of Excellence

20

Vacation villa with shared pool, golf nearby in Caribbean

Jolly Harbour / Jolly Harbour Villas

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Villa North Shore is a luxury Villa in Antigua set within lush and well-tended tropical gardens. Villa North Shore is an ideal base from which to explore the island of Antigua or make use of the many varied amenities within Jolly Harbour itself - Antigua's premier marin …see more

Certificate of Excellence

from $140 / night

$697 - $886 / week

Book View

Responds fast!
avg. 2 hours 9 minutes

from $140 / night

(1) Excellent 

19

St. Vincent and the Grenadines Vacation yacht rental

St. Vincent and the Grenadines / Mayreau

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
A Private Yacht: KALIMBA, A 2012 Beneteau Oceanis 45 foot. This private yacht, with skipper, will take you on the cruise of a lifetime around the spectacular Grenadine Islands. Starting from Grenada, or picking you up at the location of your choice, the itinerary is up …see more

from $633 / night

$3,798 / week

Book View

from $633 / night

12

Caribbean Vacation home rental

Saint John Parish / Buckleys

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Villa Sur Colline is a unique luxury villa nestled on the hilltop of Mc Guire Park. This private lush villa boast 180 degree views of the rolling hills of Buckleys. Relax with cocktails on the large deck or plan an Al fresco dinner in the outdoor gazebo. The entire pr …see more

from $135 / night

$945 / week

Book View

from $135 / night

(4) Excellent 

23

Vacation apartment rental

Kralendijk / Belnem

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
This luxury apartment located at the small, intimate, cosy and quiet complex called Belair has a gorgeous view over the crystal clear caribbean ocean and Klein Bonaire. Perfect for scuba diving and snorkeling far away from the stress of daily life. Step out of your room …see more

from $195 / night

$1,320 - $2,092 / week

Book View

Responds fast!
avg. 3 hours 3 minutes

from $195 / night

(10) Excellent 

14

Vacation villa in Martinique

Arrondissement of Le Marin / Le Diamant

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Villa's 'Dream' with its private pool diamond face of the rock on the largest Beach in Martinique, access private beach, comfort, sans vis à vis... for an unforgettable vacation with friends or family. Rent in peace: this Villa is classified 4 keys to the label 'Key hol …see more

from $293 / night

$2,049 - $3,187 / week

Book View

from $293 / night

(4) Excellent 

39

Caribbean Vacation home rental

New Providence Island / Nassau

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
What better than to live an unforgettable moment with our loved ones at a special moment in the south? A luxurious haven on the beach, an incredible new townhouse 4 bedrooms, 3 bathrooms and a half that can easily accommodate 8 people (plus 2 flip-flops seating for kid …see more

from $695 / night

$4,595 - $9,500 / week

Book View

from $695 / night

8

Vacation villa with shared pool, golf nearby in Caribbean

St. Vincent / Calliaqua

4 14 1 night min

  • 4 bedrooms
  • sleeps 14
  • 1 night min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
The White House is a stunning Art Deco villa, with breathtaking views of Bequia and Mystique, All the bedrooms are on the ground floor The outdoor pool in the construction stages and will be completed at the end of the month. It has a fully equipped game’s room, on the …see more

from $50 / night

$350 - $2,625 / week

Book View

from $50 / night

9

Grenada Vacation apartment rental

Saint George Parish / South Coast

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Suitable for children age 5+
Its all about relaxing,but your minutes away from all the action.situated in the gated community of fort Jeudy ,St Georges The apartments sit in 'Windy Trace' as the name suggests there is always a cooling breeze coming off the Atlantic with a local beach 10 minutes wa …see more

from $88 / night

$561 - $685 / week

Book View

Responds fast!
avg. 3 hours 4 minutes

from $88 / night

30

Anguilla Vacation villa rental

West End Village / Merrywing Bay

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
SONGBIRD VILLA - Rendezvous Bay, Anguilla, British West Indies Location: Anguilla 2 - 4 Bedrooms, 4.5 Baths , Air Conditioning Bedrooms Only, Answering Machine, BBQ, Beach Chairs, Blender, Cable, Ceiling Fans, Coffee Maker, Dish Washer, Dryer, DVD, Golf, Gym, …see more

from $1,950 / night

$13,650 / week

Book View

from $1,950 / night

(2) Excellent 

17

Vacation bungalow rental

Maria Trinidad Sanchez Province / Rio San Juan

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Pet friendly
Lodge 65 m2 including a bedroom with a king size bed 2x2 Meters dressing shower and a separate toilet. Fitted kitchen bar fridge with everything needed for cooking. Living area with two sofa beds. A shower with toilet Terrace with two chairs and a table a flowery field …see more

from $41 / night

$228 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

from $41 / night

(13) Very Good 

18

Vacation cottage in Barbados

Saint James Parish / Holetown

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Car not necessary
  • Air conditioning
Location, location, location, this brand new Cottage has a lovely tropical feel - all wood including floor - louvre windows and doors give you a lovely smooth breeze which keeps you cool. Bedroom with air condition.Lovely patio - sun from late morning until sunset. Love …see more

from $105 / night

$380 - $754 / week

Book View

from $105 / night

(1) Excellent 

31

Vacation b&b with swimming pool in Caribbean

Maria Trinidad Sanchez Province / Rio San Juan

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
We are a French couple and we live in the Dominican Republic for several years. Our villa is located on the heights of Rio San Juan, in a magnificent private and secure. The house has electricity 24h / 24 and free wifi connection. We love to receive and exchange with vi …see more

from $46 / night

$285 / week

Book View

Responds fast!
avg. 3 hours 6 minutes

from $46 / night

19

Bahamas Vacation cottage rental

Eleuthera / Spanish Wells

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
The cottage is ideally situated. 2.5 miles of stunning beach. Most of the time, you will be alone, and if it gets crowded, you may have two to six people around... On this part of this beach, at low tide, the ocean is a magnificent turquoise lagoon. Everything is in t …see more

from $240 / night

$1,300 - $2,215 / week

Inquire View

from $240 / night

(6) Excellent 

13

Caribbean Vacation villa rental

Iles des Saintes / Terre-de-Haut

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Very rare product at the Saintes: House renovated in 2013 with a lot of taste.All modern comforts for this beautiful villa 50 metres from the beach. Very nice terrace 150 m² teak. Fully equipped kitchen with washing machine, dish washer and dryers, modern lounge with in …see more

from $313 / night

$1,822 - $2,300 / week

Book View

from $313 / night

5

Vacation studio in Martinique

Arrondissement of Le Marin / Le Marin

Studio 2 1 night min

  • Studio
  • sleeps 2
  • 1 night min
  • Child friendly
Spacious studio with a terrace of 10 m2 Located 5 minutes from the marina Marin, shops, and 10 minutes from the most beautiful beaches with white sand of the south (tip of the sailor - Salines, macabou). Studio equipped (fridge, coffee machine, kettle, microwave, TV, so …see more

from $32 / night

$228 / week

Book View

from $32 / night

9

Vacation villa in Antigua and Barbuda

Saint John Parish / St. John's

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa #3 is a self contained unit which gives you the feeling that you are in tranquil area. Ten minutes away from St, John's but feels like you are in a secluded area. Shared swimming pool and generator and within five minutes from the closest beach. How would you lik …see more

from $225 / night

$1,575 / week

Book View

from $225 / night

16

Apartment rental in Martinique

Arrondissement of Le Marin / Trois-Ilets

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
F3 apartment of 100m2 standing, in a gated residence at Anse Mitan aux Trois Ilets enjoying a very large terrace to enjoy the outdoors, admire the view of the sea at 360 ° A 2 min walk from the beach and the pier for the maritime shuttle to Fort de France. Close to many …see more

from $103 / night

$615 / week

Book View

Responds fast!
avg. 33 minutes

from $103 / night

(5) Good 

10

Vacation home in Caribbean

Grande-Terre Island / Saint Francois

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
* Come and enjoy your holiday in this charming villa in the very heart of the Guadeloupe campaign! * You can enjoy the beach of casting, Golf, marina which are located 5 minutes from the villa! We are located just east of Guadeloupe in the beautiful seaside town o …see more

from $57 / night

$342 - $662 / week

Book View

from $57 / night

(12) Very Good 

24

Vacation home with swimming pool in Barbados

Saint James Parish / Holetown

5 11 5 nights min

  • 5 bedrooms
  • sleeps 11
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 300 mi
  • Swimming pool
Cherry Tree villa is in The centre of Holetown in St James within 5 minute walking distance to the lovely sandy beaches of the platinum coast with access to the boardwalk which you can walk along to Sandy lane . The villa is situated close to the duty free shopping m …see more

from $446 / night

$3,119 - $3,788 / week

Book View

Responds fast!
avg. 2 hours 23 minutes

from $446 / night

(11) Excellent 

26

Vacation gite in Guadeloupe

Marie-Galante / Saint Louis

4 4 3 nights min

  • 4 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Les Palmes du Moulin sont heureux de vous accueillir dans leurs locations et hébergements. Profitez du Studio Menndé dans un jardin tropical avec piscine. Découvrez ou re-découvrez l'île de Marie-Galante, entre nature sauvage et paysages envoûtants. Le logement Le bun …see more

from $114 / night

$798 / week

Book View

Responds fast!
avg. 2 hours 51 minutes

from $114 / night

Also consider