50 Best Vacation Rentals in Madeira Islands - Holiday Lettings - Cabins

Close

View larger map

Also consider

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

1,896 Vacation rentals

(4) Excellent 

28

Apartment accommodation in Madeira Islands

Madeira Islands / Porto Santo Island

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Car not necessary
Fully equipped apartment with internet wifi free, near the beach and breathtaking panoramic sea the apartment the comfortable apartment equipped with all amenities. Pleasant and contemporary decoration. Area quiet. Magnificent panoramic view on the sea. It is near (250 …see more

from $65 / night

$450 - $647 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from $65 / night

(3) Very Good 

27

Madeira Islands Vacation home rental

Calheta / Ponta do Pargo

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Child friendly
Villa Montemar is the perfect spot to recharge energies and find peace among the comfort of a home away from home. It is a 2 bedroom house prepared to receive 4 people. The Kitchen is fully equipped... You will certainly find everything you need for a perfect stay. Vill …see more

from $45 / night

$394 - $552 / week

Book View

Responds fast!
avg. 3 hours 17 minutes

from $45 / night

(3) Excellent 

43

Vacation home rental

Madeira / Funchal

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Ask about children
The apartment is ideal for groups up to 2 people. Apartment Dragoeiro has one bedroom with two single beds and a wardrobe, a large living room area with a Led TV, sofa, table, etc., a bathroom and a kitchen. The kitchen has all the necessary utensils including microwav …see more

from $38 / night

$261 / week

Book View

Responds fast!
avg. 2 hours 30 minutes

from $38 / night

24

Madeira Islands Vacation home rental

Madeira / Funchal

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Child friendly
The house in situated in Funchal , contains two bedroom one bathroom ,living room,dining room,kitchen and a beautiful terrace with city and bay views. The place is realy quiet and the neighbourhood very friendly. Around the property is lots of diferente places you can v …see more

from $65 / night

$450 / week

Book View

from $65 / night

(9) Excellent 

Certificate of Excellence

23

Vacation villa with shared pool, golf nearby in Madeira Islands

Madeira / Calheta

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Offering outstanding 360º panoramic views of the sea and mountains, Casa do Julio is a traditional Madeiran house wonderfully located on a bluff overlooking Calheta beach, yet very private and tranquil. The owner has furnished it beautifully combing contemporary furnitu …see more

Certificate of Excellence

from $131 / night

$916 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from $131 / night

(9) Excellent 

Certificate of Excellence

19

Vacation home in Madeira Islands

Calheta / Arco da Calheta

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Panoramica, 4 bedrooms,large swimming pool ,with unbelievable seaview A 4 bedroom luxury villa located in Arco da Calheta. the property has 4 luxury modern style bedrooms, 3 luxurious modern bathrooms and an open-garden bathroom with shower new modern kitchen, lau …see more

Certificate of Excellence

from $147 / night

$1,026 - $1,342 / week

Book View

from $147 / night

(27) Excellent 

Certificate of Excellence

25

Apartment rental in Madeira Islands with shared pool

Madeira / Funchal

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sunny and peaceful location with direct access to the beach. The apartment is situated in Funchal, at Formosa beach, with an amazing view over the Atlantic Ocean and direct access to the beach and surrounded by gardens. To profit the mild climate of Madeira island, you …see more

Certificate of Excellence

from $113 / night

$789 - $1,218 / week

Book View

Responds fast!
avg. 1 hour 26 minutes

from $113 / night

46

Vacation home in Faja da Ovelha

Calheta / Faja da Ovelha

3 5 4 nights min

  • 3 bedrooms
  • sleeps 5
  • 4 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Private garden
The "Casa do Leão" is the ideal place for a peaceful and luxurious stay in Madeira. Located on a Hillside in Fajã da Ovelha, you will be able to observe the Atlantic Ocean as well as the sunset all throughout the house, mainly on its three balconied or even from the gar …see more

from $68 / night

$473 / week

Book View

Responds fast!
avg. 17 minutes

from $68 / night

(5) Excellent 

28

Vacation villa in Madeira Islands

Ponta do Pargo / Serrado

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 20 mi
  • Child friendly
  • Ask about pets
Fantastic villa and garden in a stunning location perched on top of the dramatic cliffs at the western tip of this delightful island The Quinta offers two large double rooms on the ground floor and one room up in the tower - all with 4 poster beds - all with ocean view. …see more

from $182 / night

$1,270 - $2,341 / week

Book View

from $182 / night

(18) Excellent 

Certificate of Excellence

44

Beach hut rental in Madeira Islands with swimming pool

Calheta / Jardim do Mar

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
"HOUSE WHERE THE MOUTINES MEET THE SEA» The villa, is called the "house where the mountain meets the sea" because of, in one house, can enjoy at the same time, the sea and the rustic mountain nature, this because the 1st floor is the pool area and solarium where you can …see more

Certificate of Excellence

from $124 / night

$867 / week

Book View

Responds fast!
avg. 2 hours 1 minutes

from $124 / night

22

Vacation home accommodation

Calheta / Paul do Mar

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
Casa do Porto, A charming seaside home right at the sea. Casa do Porto is a typical fisherman home right at the ocean front. The village of Paul do Mar still fishes for the locals and you can go and experience the fisherman arriving and the selling of the fish right o …see more

from $40 / night

$277 - $561 / week

Book View

from $40 / night

(9) Excellent 

Certificate of Excellence

29

Prazeres Vacation villa rental

Calheta / Prazeres

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 6 mi
  • Swimming pool
  • Child friendly
This superb, very large luxury 4-bedroomed villa with pool is set within an expansive garden and lawn in a quiet and tranquil location with superb uninterrupted views of the slopes and ocean. Located in Prazeres close to facilities, it offers easy access to the express …see more

Certificate of Excellence

from $127 / night

$884 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from $127 / night

(1) Excellent 

20

Estreito da Calheta Vacation home rental

Calheta / Estreito da Calheta

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bedrooms, 3 bathrooms, separate WC, sleeps 8 Casa Frangipani is an outstanding modern villa standing on a large level site in the hamlet of Estreito da Calheta on the south-west coast of the beautiful sub-tropical island of Madeira. Designed in a contemporary style b …see more

from $240 / night

$1,687 / week

Book View

from $240 / night

(13) Very Good 

38

Estreito da Calheta Vacation villa rental

Calheta / Estreito da Calheta

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Villa Murphy is situated in a typical rural area of Madeira. Panoramic sea views are simply breathtaking. The Villa offers two bedrooms; both bedrooms are large rooms with frenchdoors leading onto the top balcony. The views are spectacular. The balcony is large and spac …see more

from $74 / night

$516 - $878 / week

Book View

Responds fast!
avg. 3 hours 6 minutes

from $74 / night

(6) Excellent 

18

Vacation home with swimming pool in Madeira Islands

Calheta / Arco da Calheta

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxurious village located near everything you need. Amazing sunset view just for who love nature. House of two floors with 5 bedrooms, 5 bathrooms, a living room and dining r / c open space. Garden overlooking the sea, terrace overlooking the sea and mountains, barb …see more

from $254 / night

$2,036 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from $254 / night

20

Vacation home rental

Madeira / Santa Cruz

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Suitable for children age 5+
Villa Vista Mar is a wonderful large high quality 3 bedroom villa that sleeps up to 6 people. It is conveniently located 1km from Funchal Airport in the town of Santa Cruz and boasts panoramic views of the coastline down to Sao Pedro. The property is private and g …see more

from $155 / night

$966 / week

Book View

from $155 / night

(7) Very Good 

Certificate of Excellence

23

Vacation cottage in Arco da Calheta

Calheta / Arco da Calheta

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 3 mi
  • Child friendly
Set in the lovely garden that is a veritable sun trap, this beautifully restored stone cottage is superbly positioned on the cliff top with outstanding views of the sea and coastline. Perfect for those that wish to experience the traditional Madeira lifestyle and be clo …see more

Certificate of Excellence

from $12 / night

$79 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from $12 / night

11

Madeira Islands Vacation home rental

Calheta / Faja da Ovelha

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Nearest beach 9 mi
  • Child friendly
  • Pet friendly
Raposeira Chloe is a typical house from Madeira built recently, in a country setting, quiet and cozy own to rest and feel nature. It is prepared for all types of guests: the nature lovers can hike or walk on trails that are taken at the place. Your preference is the mo …see more

from $36 / night

$253 / week

Book View

Responds fast!
avg. 44 minutes

from $36 / night

(3) Excellent 

23

Apartment rental in Madeira Islands

Madeira / Canical

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Our room is excellently furnished and designed to detail the host. We favor the concept of family/group of friends with room for this leisure and comfort. Can make two fantastic walks, the Bay of Open and Machico. It has walking access to both. No need to rent car, mi …see more

from $51 / night

$271 / week

Book View

from $51 / night

(1) Very Good 

12

Vacation apartment in Madeira Islands

Madeira / Machico

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
The appartement is 5minutes from the aereoport ,2 minutes from the golden beach of Machico , 20 minutes from the Funchal city , Madeira is a beautiful Island to visit . The weather in the winter minimum 15 graus .. Summertime 30 To35 ,you can swim from April to end Sep …see more

from $39 / night

$271 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

from $39 / night

41

Calheta Vacation home rental

Madeira / Calheta

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
R&B Residence is a private rental full-equipped house located in a peaceful area in Calheta, the warmest area on the southwest coastline with a beautiful marina and two man-made golden sandy beaches. We are between the crowd and the nature. R&B Residence is a perfect ho …see more

from $57 / night

$395 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from $57 / night

(1) Excellent 

33

Vacation home in Ponta Do Sol

Madeira / Ponta Do Sol

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 3 mi
  • Child friendly
  • Private garden
The typical Madeiran home with more centenary, recently refurbished, keeping its original features. It is inserted in an area where predominates the cultivation of bananas, fruit typical of the region. It is 5 minutes from Ribeira Brava near the beach and taken. Space i …see more

from $25 / night

$198 - $395 / week

Book View

from $25 / night

(1) Excellent 

14

Vacation villa rental

Porto Santo Island / Campo de Baixo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Integrated in the prestigious condominium Vilas do Espirito Santo, the villa is new and has two floors, the ground floor consists of the kitchen, fully equipped, living room and Dining and social WC. On the first floor we have two bedrooms, one with a double bed and the …see more

from $74 / night

$513 / week

Book View

Responds fast!
avg. 1 hour 55 minutes

from $74 / night

(1) Excellent 

24

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about pets
  • Private garden
The Tree is a unique piece of art. It is a place where even corners have a special touch. It is the place in which it’s possible to sleep inside art and beauty allied with sustainability and design. Super cozy! The house was built with recycled materials such as, bottle …see more

from $74 / night

$496 / week

Book View

from $74 / night

(10) Excellent 

38

Cottage rental in Madeira Islands

Ponta Do Sol / Canhas

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
ENG// Booking is for all property, so will not be anyone else on the property. It has parking for several cars, a large (heated - extra cost €20 per day) swimming pool, barbecue, and snooker. The "Casa Pereira", although is in a quiet location, in secondary road but …see more

from $169 / night

$1,182 / week

Book View

from $169 / night

(29) Very Good 

Certificate of Excellence

33

Home rental in Madeira Islands

Calheta / Estreito da Calheta

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
This old stable is beautifully refurbished and has a cool patio under the vines. The area around is mainly farmed and perfect if you would like to stay close to the beach. The house consist of 2 bedrooms upstairs (both with double beds). Downstairs you have the sittin …see more

Certificate of Excellence

from $40 / night

$278 / week

Book View

Responds fast!
avg. 2 hours 58 minutes

from $40 / night

(2) Very Good 

16

Apartment rental in Madeira Islands with shared pool, golf nearby

Funchal / Sao Goncalo

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxurious 1 & 2 bedroom Apartments furnished to the highest standard in Funchal, Portugal …see more

from $183 / night

$1,278 / week

Book View

Responds fast!
avg. 54 minutes

from $183 / night

29

Villa rental in Madeira Islands with swimming pool

Calheta / Arco da Calheta

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
*** New photos showing property renovation in January 2018. New Television (Curve screen, HD, internet connected). Our Villa is located in the rural southwest of Madeira, near Arco da Calheta, 40 minutes from Funchal airport. It is only a 5 minute drive away from the g …see more

from $156 / night

$1,092 - $2,889 / week

Book View

Responds fast!
avg. 2 hours 4 minutes

from $156 / night

(1) Excellent 

14

Home rental in Madeira Islands with golf nearby

Calheta / Estreito da Calheta

1 3 5 nights min

  • 1 bedroom
  • sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
1 bedroom and a sofa bed to sleep 3 in a quiet place, in Madeira... - Full kitchen - 2 bathrooms - Very quiet, - Isolate paradise - Barbecue - Sun chairs - Patio chairs and table - Near to Hotel Jardim Atlantico - WI-FI internet free Travel: airport at 35 minut …see more

from $62 / night

$434 / week

Book View

from $62 / night

(8) Very Good 

10

Calheta Vacation villa rental

Madeira / Calheta

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Swimming pool
  • Child friendly
Cottage modern style used for vacation, located 2 km from the sea, in a quiet area overlooking the sea. Great outdoor space to enjoy the sunny afternoons, which includes pool and Jacuzzi and even a barbecue. The house has wi-fi internet. House in a very quiet location …see more

from $102 / night

$670 - $1,143 / week

Book View

Responds fast!
avg. 1 hour 56 minutes

from $102 / night

11

Vacation cottage in Madeira Islands

Madeira / Sao Vicente

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Pet friendly
This holiday rental cottage is set in rural rustic scenery, surrounded by organic agricultural fields where seasonal aromatic herbs and vegetables are grown.The cottage was a ‘palheiro’ originally, a type of warehouse used to shelter livestock, and store agriculture too …see more

from $29 / night

$198 - $316 / week

Book View

Responds fast!
avg. 3 hours 17 minutes

from $29 / night

17

Vacation villa in Funchal

Madeira / Funchal

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Child friendly
  • Private garden
Spectacular villa with breath taking views over the ocean,the entire Funchal bay and mountains. enjoy sunrise to sunsets. the street cul de sac ,very quiet ,just two houses. this contemporary villa features an all glass facade and varanda you can see the cruis …see more

from $215 / night

$1,499 / week

Book View

from $215 / night

(1) Very Good 

17

Villa rental in Gaula with swimming pool

Madeira / Gaula

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fantastic villa on 1200 m2 plot with beautiful garden and swimming pool 14 x 6 mtr Vrij ocean views. Located 10 minutes away from the airport of madeira in the village of Gaula parking (private) the House is equipped with a professional kitchen with among other large mi …see more

from $193 / night

$1,351 / week

Book View

from $193 / night

(10) Excellent 

24

Vacation home in Madeira Islands

Calheta / Estreito da Calheta

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Gulf Stream waters lap the shores of Madeira resulting in fantastic summers and mild winters making the island an exquisite holiday destination all year round. Our spacious cottages enjoy a privileged location in Estreito da Calheta which is to be found on the sunny wes …see more

from $85 / night

$591 / week

Book View

from $85 / night

13

Quinta Grande Vacation apartment rental

Camara De Lobos / Quinta Grande

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Air conditioning
It is 2 minutes walk from the cable girao viewpoint. With fantastic views over Funchal chamber sea wolves etc. It is a very large apartment with excellent access and best wood views. It has air conditioning, barbecue, washing dryer and washing machine. full kitchen. WiF …see more

from $68 / night

$394 / week

Book View

from $68 / night

(5) Very Good 

37

Madeira Islands Vacation cottage rental

Calheta / Arco da Calheta

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
Stone rocks house with 1 bedrooms. Capacity one double bed 1 bathroom. BBQ, beautiful direct ocean view close to levadas, pool. big garden with flowers of 2000 m2 Madeira self catering : Madeira self catering book holiday homes in Portugal Madeira book villas in …see more

from $51 / night

$355 / week

Book View

from $51 / night

(3) Very Good 

51

Villa rental in Madeira Islands with golf nearby

Calheta / Arco da Calheta

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Large balcony, terrace and very big glass windows to watch and enjoy all day sunshine and sunsets of sun go down over the sea. Sleeps 8 - 4 bedrooms. Our beautiful stone Villa 'Sunshine' is just 25 minutes drive from Funchal on excellent motorway - Via Rapida. Our frien …see more

from $100 / night

$695 / week

Book View

from $100 / night

(3) Very Good 

27

Vacation villa with shared pool, golf nearby in Madeira Islands

Calheta / Prazeres

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
Purposely designed for holiday rentals to include the most sought after features, and located on the rolling hills below Prazeres, the air-conditioned 5-bedroom Eden Nature Villa has outstanding panoramic views over the green countryside to the sea and coast, an inside/ …see more

from $131 / night

$916 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from $131 / night

24

Villa rental in Campo de Baixo with golf nearby

Porto Santo Island / Campo de Baixo

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Child friendly
Villa 10 with a little garden, have DIRECT and PRIVATE ACCESS to the Beach Villa 10 is located in a private luxury community with doorman completely fenced. The beach “Praia do Ribeiro Salgado” have blue flag and is far 75 meters from the house, through a private grove …see more

from $57 / night

$395 - $1,263 / week

Book View

from $57 / night

(8) Very Good 

Certificate of Excellence

24

Vacation cottage in Madeira Islands

Madeira / Porto Moniz

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 4 mi
  • Child friendly
If you want to get away from it all then Casa Do Campo is the perfect retreat for you. Nestled in the hills and countryside, this rustic 2 bedroom cottage will allow you to while away your time without the hustle and bustle of everyday life. A short drive takes you to t …see more

Certificate of Excellence

from $43 / night

$300 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from $43 / night