Cycling holiday villas and apartments Caribbean

Close

View larger map

Also consider

North America Holidays
178701 properties
Caribbean Holidays
29023 properties
Villas St. Barts
6,291 properties
Villas St. Maarten - Saint Martin
3,629 properties
Villas Barbados
3,401 properties
Villas Dominican Republic
3,170 properties
Villas Jamaica
2,454 properties
Apartments Puerto Rico
1,690 properties
Villas Guadeloupe
953 properties
US Virgin Isles
942 properties
Villas Bahamas
817 properties
Villas Aruba
648 properties
Villas St. Lucia
578 properties
Apartments Martinique
546 properties
Houses Antigua and Barbuda
502 properties
Villas British Virgin Isles
495 properties
Villas Anguilla
458 properties
Holiday rentals Turks and Caicos Islands
446 properties
Houses St. Vincent and the Grenadines
443 properties
Villas Curacao
348 properties
Villas Grenada
255 properties
Houses Trinidad and Tobago
231 properties

Caribbean

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

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

986 Holiday homes

Filters applied: Cycling holidays (986)

Travellers going to Caribbean are booking December dates now. Secure your holiday home today and have the perfect trip.

(16) Very Good 

52

Basse-Terre Island / Deshaies

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £78 / night

£542 / week

Book View

from £78 / night

(1) Excellent 

22

Holiday apartment with shared pool in Caribbean

Saint Peter Parish / Mullins

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
Vuemont is a relatively new residential community located on a ridge overlooking the north-western coast of Barbados. The location offers something for everyone as it is ideally situated with easy access to both the West and East coasts of the Island. The charming Speig  …see more

from £95 / night

£574 - £749 / week

Book View

from £95 / night

(2) Average 

20

Samana Province / Las Terrenas

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

 …see more

from £16 / night

£106 - £241 / week

Book View

from £16 / night

Featured properties

(1) Excellent 

24

Villa rental in Antigua and Barbuda with golf nearby

Saint John Parish / St. John's

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Tamarind Villa No. 8, one of the most exclusive and luxurious 4 bedroom villas in Antigua. The villa is situated on a sunset facing bluff between two of Antigua's most beautiful beaches and is located in the exclusive Tamarind Hills community• Holiday ty  …see more

from £630 / night

£4410 - £5760 / week

Enquire View

from £630 / night

(12) Excellent 

18

Holiday villa with pool in Casuarina Estate

Bottom Bay / Casuarina Estate

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
“FANTASTIC” My wife and I stayed at the villa from 02/09/2013 to 30/09/2013, of all the places we have stayed in Barbados this is the first place we have re-booked for the following year. First of all the photographs do not do the place justice, it  …see more

from £96 / night

£450 - £675 / week

Enquire View

from £96 / night

24

Holiday villa with swimming pool in St. Lucia

Gros Islet / Beausejour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Welcome to Saline Reef, a stunning 3 bedroom Cliffside villa with great views out to Martinique and Pigeon Island. This luxury 3 bedroom Saint Lucia Villa is situated in Saline Point in the exclusive Cap Estate. Saline reef is situated on Saline Point at the ve  …see more

from £512 / night

£3583 - £8819 / week

Enquire View

from £512 / night

34

Holiday apartment in Barbados

Speightstown / Mount Brevitor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool
Windsurf is one of but a few premium quality apartments newly built to exacting standards at Mount Brevitor, St Peter overlooking the West coast of Barbados. With 2 bedrooms and bathrooms well equipped kitchen with ceramic hob, dishwasher oven and large fridge freezer.  …see more

from £119 / night

£827 / week

Book View

from £119 / night

25

Holiday villa with swimming pool, golf nearby in Caribbean

Saint James Parish / Royal Westmoreland Golf Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Palm Grove 3 a beautifully appointed 4 bedroom Luxury Villa with large private pool in the exclusive 5 star gated golfing resort community of Westmoreland in St. James, Barbados. Tucked away within the beautiful Royal Westmoreland Estate this charming 4 bedro  …see more

from £473 / night

£3308 - £11024 / week

Enquire View

from £473 / night

20

Holiday villa with swimming pool, golf nearby in Caribbean

Cap Estate / Sea Breeze Hills

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
Welcome to Cayman Villa an ultra luxurious 4 bedroom villa situated high on Sea Breeze hills in the exclusive Cap Estate with views of the Atlantic Ocean.• Board: Self Catering  …see more

from £1103 / night

£7717 - £9646 / week

Enquire View

from £1103 / night

(1) Excellent 

25

Grande-Terre Island / Saint Francois

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £145 / night

£1009 / week

Book View

from £145 / night

(3) Excellent 

9

La Altagracia Province / Bayahibe

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £55 / night

£295 - £463 / week

Book View

from £55 / night

(6) Very Good 

32

Caribbean holiday apartment rental

Saint Peter Parish / Speightstown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Well equipped apartment right opposite beach” The apartment was exactly as described & was large, bright & well equipped making it ideal for a self catering holiday, especially if you want a fairly quiet & relaxing holiday experience. Speightstown is  …see more

from £84 / night

£583 / week

Book View

from £84 / night

(9) Excellent 

29

Villa rental in Caribbean with swimming pool

Samana Province / Las Galeras

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
Gorgeous caribbean vacation villa comfortably accommodates 8 (2 king and 2 queen beds). Ocean views from every room. Large kitchen. Pool. WiFi. Security 24/7 and maid (5h/day) BBQ. Library. Serenity. Five min. to El Frances Beach, 15 min. to Rincon and La Playita Beach.  …see more

from £95 / night

£599 - £1497 / week

Book View

from £95 / night

24

Holiday villa with swimming pool, golf nearby in St. Kitts and Nevis

Nevis / Charlestown

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
Sitting proudly on the side of the Stewart's Estate and with the backdrop of Mount Nevis stands Eternity. This is a stunning 4 bedroom 3,700 sq foot modern style villa with private pool and stunning views of the Caribbean Ocean and dormant volcano of Nevis peak. This lu  …see more

from £2213 / night

£15489 - £48504 / week

Enquire View

from £2213 / night

(8) Excellent 

22

Holiday villa in Caribbean

Saint Elizabeth Parish / Treasure Beach

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Modern spacious fully furnished 2 double bedrooms (sleeps up to six) villa to rent in the town of Junction, St Elizabeth, in Jamaica's Countryside on the South Coast of the Island. Light bright and airy. Located on a private hill with breath taking views all aro  …see more

from £47 / night

£329 - £665 / week

Book View

from £47 / night

(1) Average 

24

Holiday villa in Caribbean

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Welcome to Mumbai located in Shore Pointe, one of the newest and most exquisite developments and situated directly on the stunning beach at Cupecoy. This spectacular 3 bedroom ultra luxurious fully air conditioned property with private offers the most incredible views o  …see more

from £641 / night

£4489 - £12205 / week

Enquire View

from £641 / night

(4) Excellent 

19

Puerto Rico / Culebra

2 4 nights min

  • Sleeps 2
  • 4 nights min
  • Nearest beach 0.8 km
  • Air conditioning

 …see more

from £99 / night

£591 / week

Book View

from £99 / night

(3) Excellent 

15

Holiday apartment rental

Montego Bay / St James, Montego Bay

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly
“Absolutely amazing, perfect stay no trouble no regrets” My stay at westgate hills was truly a home away from home, on arrival at the property I was greeted by the caretaker wilbert one of the nicest people you will ever meet the house is beautiful a  …see more

from £70 / night

£320 - £425 / week

Book View

from £70 / night

(1) Excellent 

19

Holiday villa rental

West End Village / Merrywing Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
Beach Front, Resort Lifestyle, Golf Club Property, 18 hole, Luxurious, 5 star resorts, Worlds Best Beaches, Stunning Ocean Views, Infinity Pool, Hot Tub,: Beachfront and On Golf Course Greg Norman 18-hole - Book now ask Steve for Special!  …see more

from £2441 / night

£17087 / week

Book View

from £2441 / night

20

Holiday cottage with shared pool, golf nearby in Caribbean

Saint James Parish / Prospect

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
Cottage 4West Coast beachfront property newly renovated and tastefully appointed. Clean, comfortable, spacious, open concept, all new interior/exterior. Master bedroom looks out directly to the sea. Large sailing vessels, yachts and luxurious cruise ships freque  …see more

from £282 / night

£1969 - £2205 / week

Book View

from £282 / night

(11) Very Good 

12

Puerto Rico / Ponce

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from £78 / night

£530 - £1357 / week

Book View

from £78 / night

35

Home rental in U.S. Virgin Islands

St. Croix / Frederiksted

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Outdoor seating/dining for 30. Come play in the sun. Enjoy the 1st US underwater park at Buck island.  …see more

from £178 / night

£1103 - £1260 / week

Book View

from £178 / night

(10) Excellent 

24

Caribbean holiday apartment rental

Saint Philip Parish / The Crane Resort

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.15 km
  • Swimming pool
“Yet again, an amazing stay!” Yet again our stay at The Crane and the Penthouse was beautifully relaxing and just what we needed. We were amazed on our return that some of the staff in the Carriage house remembered us! Everything we wanted was availa  …see more

from £139 / night

£968 - £1260 / week

Enquire View

from £139 / night

24

Holiday villa with swimming pool, golf nearby in St. Maarten-St. Martin

Sint Maarten / Cupecoy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Casa Cervo, one of the St Martin's most exquisite and luxurious Beach Front Villa. This stunning 4 bedroom ultra luxurious property with private pool has the most incredible views looking out onto Baie Rouge Bay, one of the most beautiful beaches in St M  …see more

from £941 / night

£6587 - £22048 / week

Enquire View

from £941 / night

24

Holiday villa with swimming pool in Caribbean

Saint-Martin / Terres Basses

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Located directly on beautiful Bay Rouge beach, Beau Rivage enjoys magnificent sweeping views of the beach, ocean and Anguilla. Beau Rivage's huge loggia/veranda boasts a sparkling pool, and is surrounded by comfortable single and double chaise lounges, plush seatin  …see more

from £732 / night

£5119 - £18898 / week

Enquire View

from £732 / night

17

Holiday villa with swimming pool, golf nearby in Caribbean

Antigua / Galley Bay

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Welcome to Villa Champagne, a stunning 6 bedroom villa located within the gated community of Galley Bay Heights in Antigua. Surrounded by lush vegetation, with stunning views overlooking the sea, Champagne is a spectacular tropical getaway.• Board: Self Cate  …see more

from £1445 / night

£10115 - £20256 / week

Enquire View

from £1445 / night

21

Grande-Terre Island / Sainte-Anne

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

 …see more

from £39 / night

£269 / week

Book View

from £39 / night

(1) Excellent 

24

Holiday villa with swimming pool, golf nearby in Caribbean

Cap Estate / Rodney Bay Heights

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
Welcome to Anantha Asmani, an exquisite 4 bedroom St Lucia Vacation Rental with a stunning private infinity pool at the top of the cliffs and with incredible 360 degree panoramic views of Martinique and the Pitons. Anantha Asmani is located at the very exclusive Mount d  …see more

from £1083 / night

£7579 - £10308 / week

Enquire View

from £1083 / night

22

Antigua and Barbuda holiday villa rental

Jolly Harbour / Jolly Harbour Villas

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Oceana Breeze, a stunning 4 bedroom beach front villa is situated in Jolly Harbour Beach resort in Antigua. The villa is located in a private are on a beautiful white sand beach just a few steps away from the calm turquoise Caribbean Sea.• Holiday type Family, Hon  …see more

from £1688 / night

£11812 - £16536 / week

Enquire View

from £1688 / night

(10) Very Good 

18

Holiday villa rental

Saint Philip Parish / Bottom Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“WOW” I have stayed in St. Lawrence Gap on many occasions. But on my last trip to Barbabos I discovered a villa called Edna's Court and I am glad I did. After a night of heavy partying it was a real pleasure to go "home" to Edna's Court. It's pea  …see more

from £100 / night

£833 - £1183 / week

Book View

from £100 / night

(10) Very Good 

28

Holiday apartment with shared pool, golf nearby in Caribbean

Aruba / Noord

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
This is an apartment of La Cabana BRC on the best beach of Aruba Eagle Beach a perfect place to enjoy a holliday on Aruba. Comfortable, convenient and carefree stays Room accommodations at La Cabana Beach & Racquet Club afford all the conveniences of home, s  …see more

from £79 / night

£650 - £1014 / week

Book View

from £79 / night

39

Dominican Republic holiday apartment rental

La Altagracia Province / Punta Cana

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
The activities around the resort include: Golf Course (within 3 km), Fishing, Windsurfing, Canoeing, Cycling, Diving, Horse Riding, Water Sports Facilities (on site), Water Park, Fitness Center, Spa & Wellness Center, Massage by the beach, Bicycle Rental.  …see more

from £99 / night

£591 / week

Book View

from £99 / night

12

Apartment letting in Caribbean with golf nearby

Arrondissement of Le Marin / Riviere-Pilote

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
Welcome to the sunny island of Martinique and this charming apartment, featuring a large, sunlit terrace with a hammock, perfect for relaxing in the tropical sun. The flat is set in vibrant Rivière-Pilote, which comes alive on Wednesdays and Saturdays with beach partie  …see more

from £56 / night

£273 - £336 / week

Book View

from £56 / night

(1)  

22

Holiday villa in Martinique

Martinique / Sainte Anne

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Car not necessary
  • Private garden
The Beach of Club Med is within walking distance. Salines beach is located 3 kms.Many excursions and activities are available near the villa (jet skiing, catamaran trips, tour gigs, hobby cat, scuba diving, snorkeling, glass bottom boat, offshore boat, kayak excursionTh  …see more

from £119 / night

£832 - £1589 / week

Book View

from £119 / night

12

Villa rental in Antigua and Barbuda

Antigua / Long Island, Antigua

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Sea Horse Villa, a luxury 3 bedroom beach front villa with large private pool located in the exclusive Jumby Bay Resort,Long Island Antigua.• Board: Self Catering  …see more

from £4331 / night

£30315 - £37756 / week

Enquire View

from £4331 / night

(1) Very Good 

26

Holiday apartment in Caribbean

Enterprise / Cottonbay

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Sandy Beaches is a large ground floor 2 bedroom apartment just 2 minutes walk to the nearest beach. It is a fully fitted out apartment with two bathrooms, two double bedrooms and 3 large balcony area, ideal for outdoor dining.This property has recently been ref  …see more

from £80 / night

£550 - £830 / week

Book View

from £80 / night

(12) Excellent 

13

Castle accommodation in Caribbean with swimming pool

St. George's / Petite Calivigny

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children
Circular tower in the style of a traditional Caribbean windmill for crushing sugar cane. Four poster bed. Swimming pool. Outside kitchen. Luxury furnishings. Fantastic panoramic views of the sea and mountains.We advise hiring a car although many guests have managed with  …see more

from £200 / night

£1300 / week

Book View

from £200 / night

10

Caribbean holiday apartment rental

New Providence Island / Nassau

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Car not necessary
  • Air conditioning
Nassau accommodation, Vacation Rental, Bahamas getaway, 1 bedroom, private bath, near the beach, near shopping, grocery store, banking, casinos, nightlife, near airport, near marina, yacht,  …see more

from £154 / night

£1024 / week

Book View

from £154 / night

(1) Very Good 

35

Holiday villa with swimming pool in Dominican Republic

Puerto Plata Province / Sosua

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Stunning views, a garden with tropical plants will not leave anyone indifferent.  …see more

from £43 / night

£295 - £1121 / week

Book View

from £43 / night

(2) Very Good 

21

Holiday villa with swimming pool in Caribbean

Basse-Terre Island / Lamentin

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
The villa is located in the center of Guadeloupe between Basse-Terre and Grande-Terre giving you access to the most famous sites like La Soufriere, Carbet falls but also to all the best white sands beaches in Deshaies, Gosier and Sainte-Anne, all within 60 mns drive.A c  …see more

from £140 / night

£977 / week

Book View

from £140 / night