Holiday Homes in Summerland Key

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Summerland Key holiday homes

A heated pool

Holiday Home in Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
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
Beach towels

Holiday Home in Cudjoe Key

Relax by Florida Keys Beaches, just a 7-min drive away
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
House

Holiday Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is €653
includes taxes & fees
28 Jan - 29 Jan
Starlight Serenity - Hideaway w Stunning Views
Outdoor dining

Holiday Home in Cudjoe Key

135 Waterfront Property, Boat Dock, Heated Pool, Ocean 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
Exterior

Holiday Home in Cudjoe Key

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
9.4 out of 10, Exceptional, (101 reviews)
"Great location. "
United States
Davian k.
The price is €548
includes taxes & fees
22 Jan - 23 Jan
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool

Holiday Home in Cudjoe Key

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
The price is €546
includes taxes & fees
27 Jan - 28 Jan
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Outdoor pool, a heated pool

Holiday Home in Cudjoe Key

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
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!
Exterior

Holiday Home in Cudjoe Key

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is €533
includes taxes & fees
15 Jan - 16 Jan
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Exterior

Holiday Home in Cudjoe Key

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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
Exterior

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
Outdoor pool

Holiday Home in Summerland Key

One of the very few beach houses with a daily, rental license in the Keys.
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.
A heated pool

Holiday Home in Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
2.0 star property
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
Terrace/patio

Holiday Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views
The price is €619
includes taxes & fees
28 Jan - 29 Jan
Starlight Serenity - Hideaway with Stunning Views
Pool

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
A heated pool

Holiday Home in Cudjoe Key

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
2.0 star property
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
A heated pool

Holiday Home in Cudjoe Key

Reel Island Retreat #273 at Venture Out in the Florida Keys
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
Balcony

Holiday Home in Cutthroat Harbor Estates

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
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
A heated pool

Holiday Home in Cudjoe Key

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
2.0 star property
The price is €583
includes taxes & fees
15 Jan - 16 Jan
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Exterior

Holiday Home in Cudjoe Key

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
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
Property grounds

Holiday Home in Cudjoe Key

Cudjoe Cottages, swimming pool, 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.
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Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"The rooms were great. The bunk bed mattresses could be better but after a long day the kids didn’t mind them. The room was clean and tons of room. If you want water views ask for 2nd floor and for sunrise views ask for north building. The drinks at the bar are great and the kids loved the beach and pool area. The location is great for trips to Bahia Honda and key west. Would definitely stay here again. "
Benjamin 5-night trip
Posted 4 days ago
Sugarloaf Key Hotel at KOA Resort

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