Holiday Homes in Summerland Key

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Our top choices for Summerland Key holiday homes

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2.5 star property
Cudjoe Key
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is AU$901
includes taxes & fees
19 Jan - 20 Jan
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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

Relax by Florida Keys Beaches, just a 7-min drive away
Cudjoe Key
9.8 out of 10, Exceptional, (198 reviews)
"Will definitely stay here again "
United States
Jeannine R.
The price is AU$852
includes taxes & fees
18 Jan - 19 Jan
Relax by Florida Keys Beaches, just a 7-min drive away

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is AU$1,138
includes taxes & fees
28 Jan - 29 Jan
Starlight Serenity - Hideaway w Stunning Views

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

135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
2.0 star property
Cudjoe Key
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 AU$1,018
includes taxes & fees
28 Jan - 29 Jan
135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101 reviews)
"Great location. "
United States
Davian k.
The price is AU$937
includes taxes & fees
22 Jan - 23 Jan
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
The price is AU$922
includes taxes & fees
18 Jan - 19 Jan
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
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 AU$808
includes taxes & fees
6 Feb - 7 Feb
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is AU$929
includes taxes & fees
18 Jan - 19 Jan
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
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 AU$882
includes taxes & fees
19 Jan - 20 Jan
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Southern Exposure in Cudjoe Key #49

Southern Exposure in Cudjoe Key #49
2.0 star property
Cudjoe Key
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.
The price is AU$1,039
includes taxes & fees
8 Feb - 9 Feb
Southern Exposure in Cudjoe Key #49

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

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (65 reviews)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is AU$1,768
includes taxes & fees
25 Jan - 26 Jan
One of the very few beach houses with a daily, rental license in the Keys.

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
2.0 star property
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is AU$1,143
includes taxes & fees
18 Jan - 19 Jan
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Azucar - Beach Houses Key West

Azucar - Beach Houses Key West
Sugarloaf Key
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.
The price is AU$3,749
includes taxes & fees
19 Jan - 20 Jan
Azucar - Beach Houses Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
2.0 star property
Cudjoe Key
The price is AU$1,003
includes taxes & fees
19 Jan - 20 Jan
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

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

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

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very good, (120 reviews)
"Great experience "
United States
Peyton S.
The price is AU$934
includes taxes & fees
18 Jan - 19 Jan
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
2.0 star property
Cudjoe Key
The price is AU$996
includes taxes & fees
19 Jan - 20 Jan
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

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

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (90 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is AU$1,205
includes taxes & fees
4 Feb - 5 Feb
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
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 AU$984
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

Find out more about Summerland Key

Summerland Key Holiday Homes information

Number of reviews
998
Accommodation
411 Holiday Homes
Lowest Price
AU$808
Highest Price
AU$3,749