Holiday Homes in Summerland Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Summerland Key holiday homes

2.5 star property
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is €532
includes taxes & fees
19 Jan - 20 Jan
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
9.8 out of 10, Exceptional, (198 reviews)
"Will definitely stay here again "
United States
Jeannine R.
Relax by Florida Keys Beaches, just a 7-min drive away
2.0 star property
The price is €653
includes taxes & fees
28 Jan - 29 Jan
Starlight Serenity - Hideaway w Stunning Views
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Our house was beautiful and right on the water! Great sunrises and beautiful views! Fully equipped with everything you need or want! This home is the best VRBO we have rented! Would love to come back!!"
United States
Loretta F.
The price is €602
includes taxes & fees
28 Jan - 29 Jan
135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
9.4 out of 10, Exceptional, (101 reviews)
"Great location. "
United States
Davian k.
The price is €548
includes taxes & fees
22 Jan - 23 Jan
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
The price is €546
includes taxes & fees
27 Jan - 28 Jan
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
7.6 out of 10, Good, (13 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is €472
includes taxes & fees
4 Feb - 5 Feb
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is €533
includes taxes & fees
15 Jan - 16 Jan
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
8.8 out of 10, Excellent, (157 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is €521
includes taxes & fees
19 Jan - 20 Jan
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Holiday Home in Cudjoe Key

Southern Exposure in Cudjoe Key #49
2.0 star property
7.6 out of 10, Good, (4 reviews)
"The house is nice and sitting on the balcony feels like you're floating. It was a nice place to stay"
United States
Colleen G.
Southern Exposure in Cudjoe Key #49
8.8 out of 10, Excellent, (65 reviews)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is €1,059
includes taxes & fees
25 Jan - 26 Jan
One of the very few beach houses with a daily, rental license in the Keys.
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is €684
includes taxes & fees
18 Jan - 19 Jan
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
The price is €619
includes taxes & fees
28 Jan - 29 Jan
Starlight Serenity - Hideaway with Stunning Views

Holiday Home in Sugarloaf Key

Azucar - Beach Houses Key West
10.0 out of 10, Exceptional, (10 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
Azucar - Beach Houses Key West
The price is €597
includes taxes & fees
27 Jan - 28 Jan
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
9.6 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
Reel Island Retreat #273 at Venture Out in the Florida Keys
8.4 out of 10, Very good, (120 reviews)
"Great experience "
United States
Peyton S.
The price is €558
includes taxes & fees
18 Jan - 19 Jan
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
The price is €583
includes taxes & fees
15 Jan - 16 Jan
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
8.6 out of 10, Excellent, (90 reviews)
"We had a great time and will be back. "
United States
Michelle K.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is €582
includes taxes & fees
19 Jan - 20 Jan
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Summerland Key Hotel Reviews

Find out more about Summerland Key

Summerland Key Holiday Homes information

Number of reviews
1,000
Accommodation
411 Holiday Homes
Lowest Price
€472
Highest Price
€1,059