COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Houses Summerland Key

Updating...

age 0-16
111 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

111 houses

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$556

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$299

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$334

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Rental types

All filters match

Price per night from

$161

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$450

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$518

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$768

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$335

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$314

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$258

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$1,727

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$141

30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$162

KEY BLESSING - Experience The Keys Life, Charming 3 Bedroom Canal Front Home, Do

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$177

Reel Paradise

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$287

BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$180

New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$179

The Helms House

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$288

Sailfish Manor

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 9

Match: Rental types

All filters match

Price per night from

$314

KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$179

TARPON RANCH - Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock

Summerland Key house

6 bedrooms / 8 bathrooms / sleeps 14

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$180

New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$296

THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$180

The Pointe

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Rental types

All filters match

Price per night from

$209

BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$174

THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$174

Keys Life

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$209

THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

Match: Rental types

All filters match

Price per night from

$144

Great rentals within 20 miles that match your search

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Match: Rental types

All filters match

Price per night from

$576

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Match: Rental types

All filters match

Price per night from

$691

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$130

Angelfish Cove

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$159

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$176

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$235

Lafitte Landing

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Rental types

All filters match

Price per night from

$121

Margarita Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$161

Manatee Bay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$129

Mango House

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 4

Match: Rental types

All filters match

Price per night from

$111

Viewing 38 of 111
houses in Summerland Key

×

Also consider