Title: Summerland Key Luxury Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/6177802/bda449a1-0506-4d80-94a6-fb19766bc7f4.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Summerland Key Luxury Vacations

## Book a Luxury Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to $1,045 when you book a flight and hotel together\*
- ###  
Find the right fit  
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Plan, book, and manage your trip all in one place

## Top Luxury vacation packages in Summerland Key

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

![Hilton Cabana Miami Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/18200/18107/0760f366_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Cabana Miami Beach Resort

Mid Beach

Save 100% on your flight

$626

per person

Jun 4 - Jun 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (610 reviews)

We stayed on the penthouse floor, our room was facing the ocean it was beautiful! And housekeeping was wonderful! I would stay there again!

Reviewed on Mar 11, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,195

per person

May 14 - May 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/759b33fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### EAST Miami Residences

Brickell

Save 100% on your flight

$1,934

per person

May 13 - May 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (109 reviews)

We loved staying here and will definitely be back! Yes, it is very expensive, but compared to other Miami hotels this one is the best overall deal for what you get.

Reviewed on Mar 1, 2026

![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Villas At Hawks Cay Resort

Save 100% on your flight

$1,977

per person

May 13 - May 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (170 reviews)

Property was clean and staff were helpful. Would stay again.

Reviewed on Mar 11, 2026

![The Sunny](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145283/edbd844f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Sunny

Ocean Four

Save 100% on your flight

$667

per person

May 13 - May 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (81 reviews)

You can tell it’s been remodeled and they are working through a new re opening. Resort has a lot of potential but was not warned about $50 resort fee which is excessive for a one night stay. Rooms were clean but smelled chemical. Staff was nice.

Reviewed on Mar 12, 2026

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Luxury vacations in Summerland Key

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

![EAST Miami](https://images.trvl-media.com/lodging/13000000/12080000/12079000/12078999/007ff5b4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### EAST Miami

Brickell

Save 100% on your flight

$1,822

per person

May 13 - May 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (3,695 reviews)

Enjoyed everything.

Reviewed on Mar 12, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,195

per person

May 14 - May 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/759b33fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### EAST Miami Residences

Brickell

Save 100% on your flight

$1,934

per person

May 13 - May 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (109 reviews)

We loved staying here and will definitely be back! Yes, it is very expensive, but compared to other Miami hotels this one is the best overall deal for what you get.

Reviewed on Mar 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Luxury vacations in Summerland Key

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

![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel South Beach

South Beach

Save 100% on your flight

$1,391

per person

May 28 - May 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,455 reviews)

This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again!

Reviewed on Mar 7, 2026

![W South Beach](https://images.trvl-media.com/lodging/1000000/20000/11900/11881/486a329f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### W South Beach

South Beach

$2,911

per person

May 1 - May 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,002 reviews)

We waited 2 days and moved 2 rooms before getting our actual room. For that reason the manager upgraded us for the remainder of the week to a 4 bedroom, Oceanfront suite. The property is awesome, but the pool closing at 5:00 is annoying and then closing even earlier for private events is even more annoying. Request a room on the North side of the property to avoid early morning car honking and construction beeps at 7:00 am every day.

Reviewed on Mar 2, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,195

per person

May 14 - May 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Luxury vacations in Summerland Key

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

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

$600

per person

May 28 - Jun 1

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (1,013 reviews)

It’s totally sufficient for the type of hotel. Older but clean. Great location

Reviewed on Mar 9, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,153

per person

May 21 - May 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![President Hotel](https://images.trvl-media.com/lodging/1000000/580000/575900/575859/0052492b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel

South Beach

Save 100% on your flight

$771

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,065 reviews)

The wifi went out the 3rd day of our trip so if you didnt have a Netflix or Prime acct you wasnt getting any TV service.

Reviewed on Mar 12, 2026

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## All you need to know about luxury vacations in Summerland Key

####  What can I expect from a luxury Summerland Key vacation? 

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Summerland Key vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

####  How can I find all-inclusive luxury vacation packages in Summerland Key? 

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5\* filter to find truly sensational stays. You barely need to lift a finger. 

####  Can I book a cheap Summerland Key luxury vacation? 

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $600\. Prices and availability are subject to change. Additional terms may apply. 

####  How can I book a luxury family vacation in Summerland Key? 

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

####  Can I book a package in Summerland Key with a luxury vacation home? 

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package. 

####  How can I find the best luxury vacation deals in Summerland Key? 

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months. 

####  Can I book a luxury holiday in Summerland Key with free cancellation and/or flexible dates? 

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

####  Why should I book my luxury trip to Summerland Key with Expedia? 

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind. 

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## More Vacation Ideas

[Flights to Summerland Key

](https://expedia.com/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[

Summerland Key Hotels

](https://expedia.com/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[

Vacation Rentals in Summerland Key

](https://expedia.com/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[

Car Rentals in Summerland Key

](https://expedia.com/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[

Summerland Key Vacations

](https://expedia.com/Summerland-Key.d6177802.Destination-Travel-Guides)[

Things to do in Summerland Key

](https://expedia.com/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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