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.
Private Oasis at Arya

Private Oasis at Arya

3.5 out of 5
Coconut Grove
Save 100% on your flight
Price was $1,124, price is now $633 per person
$633
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This aparthotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $26,591, price is now $12,309 per person
$12,309
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This aparthotel features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was $5,370, price is now $2,946 per person
$2,946
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.
EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Save 100% on your flight
Price was $2,781, price is now $1,539 per person
$1,539
per person
Oct 28 - Nov 3
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury hotel features 2 restaurants, 4 outdoor pools, and a 24-hour gym. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and concierge services.
Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Save 100% on your flight
Price was $1,356, price is now $765 per person
$765
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Valet parking, a business center, and limo/town car service are also offered.

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
$148 nightly
The price is $167 total per night
$167 total
Aug 24 - Aug 25
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
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
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

3 out of 5
311 Johnson Rd Summerland Key FL
Get rates
An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Luggage storage is also provided.
Pool
Pet friendly
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
$119 nightly
The price is $134 total per night
$134 total
Aug 24 - Aug 25
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
$96 nightly
The price is $108 total per night
$108 total
Sep 2 - Sep 3
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A picnic area is also provided.
Pool
Pet friendly
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.

Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
See properties

Frequently asked questions

How much are vacation packages to Summerland Key?
With deals starting as low as $633, 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

A coastal road with a beach on one side and a marina with boats on the other.
A coastal pier extending into the sea, surrounded by rocky shores and greenery.
An aerial view of a long bridge over turquoise waters with clear visibility of the bridge's structure and vehicles.
An aerial view of a long bridge over turquoise waters with clear visibility of the bridge's structure and surrounding landscape.
A long bridge over turquoise waters with clear skies.

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