Luxury Vacations in Madeira Island 2026

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Flight and Luxury hotel deals in Madeira Island

Price found within the past 48 hours. Click for updated prices.

Pestana Casino Park Ocean and SPA Hotel

CA $585

per person

Sep 27 - Sep 30

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.6/10 Excellent! (1,001 reviews)

Good basic 4 star hotel, as a base with a pool and breakfast it was fine for us. As long as a little tired decor doesn’t trigger you you’ll be great. Location is fantastic with a small park next door, shopping centre 5mins walk away and dozens of bars and restaurants nearby.

Reviewed on Aug 6, 2026

Pestana Ocean Bay Resort

CA $1,294

per person

Sep 16 - Sep 21

found 20 hours ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.4/10 Very good! (259 reviews)

Carla and the management team was excellent.

Reviewed on Aug 14, 2026

Albatroz Beach & Yacht Club

CA $1,368

per person

Sep 16 - Sep 21

found 17 hours ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

9.8/10 Exceptional! (304 reviews)

We thoroughly enjoyed our stay at the Albatroz! This holiday experience was all that we were looking for - excellent food with exceptional service, a warm welcoming atmosphere from the front desk to the restaurant and housekeeping staff, and unparalleled attentiveness from all staff. This hotel has ‘old-world’ charm and is set in a location with amazing views, ocean pools, and beautiful gardens. This is a hidden gem - your stress level will decrease from the first moment you step onto the hotel grounds. As a bonus, it was close to the airport so we could enjoy the views of incoming and outgoing flights with little noise. We started planning our return trip while we were there and look forward to returning to the Albatroz soon!

Reviewed on Aug 10, 2026

Casa Velha do Palheiro, Relais & Chateaux

CA $1,713

per person

Sep 16 - Sep 21

found 17 hours ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

9.6/10 Exceptional! (106 reviews)

If it’s your first time in Madeira I’d suggest staying somewhere in city center, it takes 15 mins to get to this hotel. Very nice property and amenities. The staff and service is weak , shortage of staff. The breakfast buffet for a 5 starvhotel and the price was so weak as weak.

Reviewed on Aug 9, 2026

Hyatt Ziva Madeira

CA $1,131

per person

Sep 16 - Sep 21

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.8/10 Excellent! (257 reviews)

Personnels were amazing but not enough so service was slow.

Reviewed on Aug 12, 2026

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5* Luxury holidays in Madeira Island

Price found within the past 48 hours. Click for updated prices.

Pestana Casino Park Ocean and SPA Hotel

CA $585

per person

Sep 27 - Sep 30

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.6/10 Excellent! (1,001 reviews)

Reviewed on Aug 6, 2026

Albatroz Beach & Yacht Club

CA $1,368

per person

Sep 16 - Sep 21

found 17 hours ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

9.8/10 Exceptional! (304 reviews)

Reviewed on Aug 10, 2026

Casa Velha do Palheiro, Relais & Chateaux

CA $1,713

per person

Sep 16 - Sep 21

found 17 hours ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

9.6/10 Exceptional! (106 reviews)

Reviewed on Aug 9, 2026

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3 Night Luxury holidays in Madeira Island

Price found within the past 48 hours. Click for updated prices.

Pestana Casino Park Ocean and SPA Hotel

CA $585

per person

Sep 27 - Sep 30

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.6/10 Excellent! (1,001 reviews)

Reviewed on Aug 6, 2026

Pestana Ocean Bay Resort

CA $807

per person

Sep 27 - Sep 30

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.4/10 Very good! (259 reviews)

Carla and the management team was excellent.

Reviewed on Aug 14, 2026

Albatroz Beach & Yacht Club

CA $832

per person

Sep 27 - Sep 30

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

9.8/10 Exceptional! (304 reviews)

Reviewed on Aug 10, 2026

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4 Night Luxury holidays in Madeira Island

Price found within the past 48 hours. Click for updated prices.

Hotel Monte Carlo

Sao Pedro

CA $1,743

per person

Oct 10 - Oct 13

found 2 hours ago

Roundtrip flight included

Calgary (YYC) to Funchal (FNC)

7.8/10 Good! (368 reviews)

This hotel is an historical building with quite beautiful architecture. However it lacks many amenities of newer hotels such as AC, hair dryers and a fridge. The rooms and furnishings are very dated but fit into the character of the building. The area is quiet and not touristy which is nice for those who prefer this. We only ate in the restaurant for breakfast and it was pretty good. We did find ants in our room but the employees were very accommodating and made sure we were comfortable in another room.

Reviewed on Jul 27, 2025

Pestana Casino Park Ocean and SPA Hotel

CA $2,031

per person

Oct 10 - Oct 13

found 2 hours ago

Roundtrip flight included

Calgary (YYC) to Funchal (FNC)

8.6/10 Excellent! (1,001 reviews)

Reviewed on Aug 6, 2026

Hyatt Ziva Madeira

CA $2,104

per person

Oct 10 - Oct 13

found 2 hours ago

Roundtrip flight included

Calgary (YYC) to Funchal (FNC)

8.8/10 Excellent! (257 reviews)

Personnels were amazing but not enough so service was slow.

Reviewed on Aug 12, 2026

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What are some benefits when booking luxury Madeira Island vacations?

When you book a luxury Madeira Island vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Madeira Island?

If you're looking for something luxurious in Madeira Island, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $585, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 37. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Madeira Island. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Madeira Island?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Madeira Island.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Madeira Island. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Madeira Island?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Madeira Island or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Madeira Island. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Madeira Island

Reid's Palace, A Belmond Hotel, Madeira

Estrada Monumental 139 Funchal

39 min drive from Porto Moniz Natural Pools

Book a stay at this luxury hotel in Funchal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...

Hyatt Ziva Madeira

Sitio da Piedade Machico Madeira

25 min drive from Porto Moniz Natural Pools

Book a stay at this luxury hotel in Machico. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Popular attractions Madeira Whale Museum and Sao Lourenco ...

8.8/10 Excellent! (262 reviews)

"Personnels were amazing but not enough so service was slow."

Reviewed on Aug 12, 2026

The Cliff Bay, by PortoBay

Estrada Monumental 147 Funchal

39 min drive from Porto Moniz Natural Pools

Book a stay at this luxury hotel in Funchal. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...

9.8/10 Exceptional! (954 reviews)

"Fantastic hotel and stay. All staff members were extremely friendly and helpful. I was even surprised with a cake on my birthday :). The hotel bars and breakfast were all great. There are many restaurants within walking distance and there are also several restaurants at the hotel although I did not ..."

Reviewed on Aug 12, 2026

See all 5,533 properties in Madeira Island

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.