A Quiet Paradise Is Possible in Summerland Key Rentals

Come experience the quiet and blue waters of the Florida Keys from Summerland Key rentals for your next tropical adventure. Much more serene than some of the more touristy Keys, this island is the ideal getaway when you simply want to relax and absorb your surroundings.

Live the Island Life in Summerland Key Rentals


Live among the tropical birds and plants by staying in Summerland Key condos, and have the added advantage of being within walking distance to your favorite watering hole or seaside restaurant. Fresh seafood, warm weather and plenty of sunshine are virtually guaranteed to renew and recharge you when you stay in Summerland Key villas.

Relax on the Beach near Summerland Key Condos


Find your Summerland Key rentals on the beach so you can easily step out for a morning jog or evening stroll in the moonlight. Perhaps you simply want to nap or read in the sun while the kids play in the sand; Summerland Key condos let you do as much or as little as you like, providing comfortable air conditioning and private quarters any time of day.

Reserve your Summerland Key villas and enjoy simply forgetting about the world for at least a few days; a stop at the local market upon arrival will allow you to enjoy the use of your fully-equipped kitchen without interacting with others for a time.

Choose Summerland Key Villas for Your Group Outing


Family vacations are a great reason for staying in Summerland Key rentals, as everyone can have their own bedrooms and even bathrooms to avoid any feeling of crowding. Honeymooners also love the seclusion of Summerland Key villas located in the midst of the local rainforests and access to private beaches. Don’t forget that Summerland Key condos are also great for a unique family reunion, destination wedding on the beach, extended winter stay, and even working vacations or business retreats.

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Siesta Key rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.


Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Book Faster

Property Type

Cottages
Estates
Homes
Apartments
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Condos
Farmhouses
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Book Faster

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Summerland Key: Houses, Estates & More(64)

64 Results
$2,100 - $2,450
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(13)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
(15)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
31 night minimum stay
(3)
$1,595 - $2,700
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(7)
$2,000 - $2,500
per month
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night minimum stay
$285 - $375
per night
6 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 7 night minimum stay
(36)
$250
per night
6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
6 night minimum stay
(3)
$350
per night
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(9)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$19,000
per month
28 - 30 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
28 - 30 night minimum stay
(3)
  • 4 BR,
  • 2 BA,
  • Sleeps 12
$9,450
per month
28 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 2 BR,
  • 2 BA,
  • Sleeps 6
  • 3 BR,
  • 2 BA,
  • Sleeps 6
  • 3 BR,
  • 3 BA,
  • Sleeps 8
  • 2 BR,
  • 2 BA,
  • Sleeps 7
43 more choices from the HomeAway Network
$2,800
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(10)
$3,750
per month
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(3)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
28 night minimum stay
(4)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 14 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night minimum stay
(12)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(7)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
(21)
$817 - $1,600
per week
7 - 31 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 - 31 night minimum stay
(5)
Advertisement