Deals on vacations and trips to Summerland Key

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Summerland Key flight + hotel vacation packages

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

Le Particulier Miami

3.5 out of 5
Mid Beach
Price was $1,401, price is now $560 per person
$560
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, free WiFi in public areas, and a snack bar/deli. Luggage storage is provided and the front desk is staffed around-the-clock.
Iberostar Waves Berkeley Shore

Iberostar Waves Berkeley Shore

4 out of 5
South Beach
Price was $2,110, price is now $770 per person
$770
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. There's a rooftop terrace on site, and a 24-hour front desk and a terrace are also provided.
Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Price was $2,049, price is now $769 per person
$769
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This aparthotel features an outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,617, price is now $648 per person
$648
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $2,120, price is now $891 per person
$891
per person
Jan 21 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features free WiFi in public areas, concierge services, and valet parking. A terrace, a garden, and luggage storage are also on offer.

Top Summerland Key hotels deals

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$137 nightly
The price is $154 total per night
$154 total
Nov 30 - Dec 1
Total with taxes and fees
The private beach and marina are among the highlights at this motel. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Enjoy the outdoor pool and free perks like on-the-go breakfast and free self parking.
On private beach
Pool
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $111 total per night
$111 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features a marina, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free WiFi. A bar/lounge and a garden are also provided.
Pool
Parking included
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$195 nightly
The price is $219 total per night
$219 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-in, and luggage storage are also on offer.
Pool
Pet friendly
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
Get rates
The private beach and marina are among the highlights at this hotel. Enjoy the outdoor pool and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
On private beach
Pool
Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

Summerland Key FL
Get rates
This vacation home features an outdoor pool and a gym. Enjoy the hot tub and conveniences like a garden and laundry facilities.
Pool
Hot Tub
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key FL
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
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See all available properties in Summerland Key
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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.

Popular places to visit

Upper Sugarloaf Sound

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

Upper Sugarloaf Sound

Upper Sugarloaf Key

Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.

Upper Sugarloaf Key

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

Sugarloaf Beach

Frequently asked questions

How much are vacation packages to Summerland Key?
With deals starting as low as $560, flight and hotel packages are a fantastic way to make your budget stretch further. Summerland Key, here you come!
Where can I get the best vacation package deals for Summerland Key?
With around 400 air carriers and 1,000,000 hotels across the world, it's hard to top Travelocity. Take advantage of our impressive range and create your dream Summerland Key package deal. Don't you love it when vacation planning is that easy?
Why should I purchase my Summerland Key vacation bundle with Travelocity?
You'll not only save lots, but you'll also have access to our 24/7 customer support, high-quality service and a Price Match Guarantee. Wander across the world, uncover lesser-known sights and make lifelong memories — we'll take care of the little details.
Can I save money on my Summerland Key car rental if I book it with a hotel or flight?
With a Summerland Key vacation package, you can combine your car, flight and hotel bookings and save a tidy sum. If you're eager to explore the best of this fantastic location, why not make tracks to PortMiami? This famous attraction is 110 mi from Summerland Key. With your own rental car, you'll be there belong long.
What is the best time of year to go to Summerland Key?
If you'd rather avoid expensive airfares, hordes of tourists and packed hotels, organize your trip outside of January, February and March. The quietest time to visit Summerland Key is August, September and October. You'll find hotel rates are the highest in and the most economical in .
Which airport is best for Summerland Key?
The top airport for Summerland Key is Key West Intl. Airport (EYW). You'll find it 20 mi east of the downtown area.
Where should I stay when visiting Summerland Key?
If you're after someplace comfortable to base yourself, check out the Tropical Island Sanctuary. It's the top choice for many travelers.

Photos of local treasures

Browse Summerland Key vacation photos for more inspiration

Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house
Sugarloaf Shores featuring a sunset and tropical scenes
Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house

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