Vacation rentals in Summerland Key

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Top-rated vacation rentals in Summerland Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Cottage in Cudjoe Key
ATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!
Dec. 13 – 20
$1,291 CAD per night
4.92 out of 5 average rating, 130 reviews
Superhost
Tiny homes in Big Pine Key
Breezy pines 28 foot 5th wheel trailer .
Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.
Nov. 16 – 23
$187 CAD per night
4.8 out of 5 average rating, 88 reviews
Guest favourite
Home in Cudjoe Key
Sunrise Beach Escape
For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.
Jul. 11 – 18
$576 CAD per night
4.91 out of 5 average rating, 101 reviews

Popular amenities for Summerland Key vacation rentals

Stay near Summerland Key's top sights

Square Grouper Bar and Grill47 locals recommend
Tonio's Seafood Shack & Tiki Bar14 locals recommend
Galley Grill19 locals recommend
My New Joint27 locals recommend
Murray's Market16 locals recommend
Cudjoe Sales Fishermen's Warehouse4 locals recommend

Other great vacation rentals in Summerland Key

Superhost
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
Aug. 27 – Sep. 3
$709 CAD per night
4.82 out of 5 average rating, 22 reviews
Guest favourite
Home in Cudjoe Key
Conch Cabana in Paradise 23 miles outside Key West
May 28 – Jun. 4
$513 CAD per night
4.94 out of 5 average rating, 18 reviews
Guest favourite
Cottage in Cudjoe Key
King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Oct. 5 – 12
$794 CAD per night
4.9 out of 5 average rating, 73 reviews
Guest favourite
Home in Cudjoe Key
Paradise in Cudjoe! Perfect Family Home!
Oct. 30 – Nov. 6
$622 CAD per night
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Big Pine Key
Key home with open water access!!
Jan. 20 – 27
$819 CAD per night
4.86 out of 5 average rating, 58 reviews
Guest favourite
Camper/RV in Big Pine Key
Having fun in the lower Keys
Sep. 2 – 9
$263 CAD per night
4.91 out of 5 average rating, 32 reviews
Guest favourite
Home in Big Pine Key
Fishermen`s Paradise: Huge pool, 220-foot dock
Sep. 3 – 10
$1,504 CAD per night
4.89 out of 5 average rating, 62 reviews
Superhost
Home in Cudjoe Key
Venture Out -Million Dollar Island Resort
Apr. 13 – 20
$450 CAD per night
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Cudjoe Key
Sailfish Haven
Oct. 31 – Nov. 7
$468 CAD per night
4.83 out of 5 average rating, 6 reviews
Guest favourite
Vacation home in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
Nov. 27 – Dec. 4
$543 CAD per night
5.0 out of 5 average rating, 29 reviews
Guest favourite
Condo in Key West
Hidden Beach Duplex, Best Place in Key West
Nov. 17 – 24
$1,000 CAD per night
4.99 out of 5 average rating, 83 reviews
Guest favourite
Camper/RV in Big Pine Key
Delightful 1 bedroom camper with pool
Nov. 19 – 26
$291 CAD per night
4.94 out of 5 average rating, 35 reviews

Quick stats about vacation rentals in Summerland Key

Total rentals

210 properties

Rentals with a pool

140 properties have a pool

Pet-friendly rentals

90 properties allow pets

Family-friendly rentals

180 properties are a good fit for families

Total number of reviews

3.3K reviews

Nightly prices starting at

$122 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Summerland Key