Summerland Key Rentals

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163 Houses

(1) Excellent 

20

Paradise n Summerland Key Cove

Lower Keys / Summerland Key

Summerland Key house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$172

Price per night from

$172

19

Living in Paradise

Lower Keys / Summerland Key

Summerland Key house

3 6 28 nights min

  • 3 bedrooms
  • sleeps 6
  • 28 nights min
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$114

Price per night from

$114

(2) Very Good 

15

Island Living

Lower Keys / Summerland Key

Summerland Key house

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Price per night from

$225

Price per night from

$225

25

Blue weekly vacation rental, great view. Heated private Pool.

Lower Keys / Summerland Key

Summerland Key house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$393

Price per night from

$393

29

Spacious, canal front villa w/ private pool and hot tub - 3 dogs are welcome!

Lower Keys / Summerland Key

Summerland Key house

3 6 28 nights min

  • 3 bedrooms
  • sleeps 6
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$188

Price per night from

$188

19

Gone Fishing

Lower Keys / Summerland Key

Summerland Key house

3 6 28 nights min

  • 3 bedrooms
  • sleeps 6
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$211

Price per night from

$211

24

Villa Cayo

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$267

Price per night from

$267

22

Caribbean Dream

Lower Keys / Summerland Key

Summerland Key house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$200

Price per night from

$200

14

Direct Atlantic Ocean front private boat ramp dock

Lower Keys / Summerland Key

Summerland Key house

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$161

Responds fast!
avg. 3 hours 44 minutes

Price per night from

$161

13

Gulf Shores

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$100

Price per night from

$100

27

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

Lower Keys / Summerland Key

Summerland Key house

5 10 30 nights min

  • 5 bedrooms
  • sleeps 10
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$764

Price per night from

$764

(1) Excellent 

51

Oceanfront House

Lower Keys / Summerland Key

Summerland Key house

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$421

Responds fast!
avg. 3 hours 43 minutes

Price per night from

$421

21

Salty Retreat

Lower Keys / Summerland Key

Summerland Key house

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Child Friendly

Price per night from

$447

Price per night from

$447

18

Big Torch Retreat

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$100

Price per night from

$100

12

Blue Lagoon

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$200

Price per night from

$200

17

Another Day In Paradise

Lower Keys / Summerland Key

Summerland Key house

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Child Friendly

Price per night from

$268

Price per night from

$268

13

Family Friendly House In Paradise

Lower Keys / Summerland Key

Summerland Key house

5 8 30 nights min

  • 5 bedrooms
  • sleeps 8
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$210

Price per night from

$210

12

Caribbean House

Lower Keys / Summerland Key

Summerland Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$83

Price per night from

$83

14

Cove Isles

Lower Keys / Summerland Key

Summerland Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$110

Price per night from

$110

18

Cruikshank

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$168

Price per night from

$168

13

Casa Turquesa

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$207

Price per night from

$207

17

Paradise Palms

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$170

Price per night from

$170

Great rentals within 20 miles that match your search

Distance approx 2.81 km from Summerland Key Show on Map

13

Waterside Bay

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 28 nights min

  • 3 bedrooms
  • sleeps 6
  • 28 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$196

Price per night from

$196

Distance approx 5.08 km from Summerland Key Show on Map

(1) Excellent 

20

Fisherman's Paradise in the Heart of Big Pine Key

Florida Keys / Big Pine Key

Big Pine Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly

Price per night from

$113

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$113

Distance approx 3.62 km from Summerland Key Show on Map

16

Charming Elevated Waterfront Home

Florida Keys / Big Pine Key

Big Pine Key house

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$163

Responds fast!
avg. 3 hours 2 minutes

Price per night from

$163

Distance approx 2.47 km from Summerland Key Show on Map

13

Shark Hideaway, Boating Canal and Sunset Views

Florida Keys / Cudjoe Key

Cudjoe Key house

1 2 28 nights min

  • 1 bedroom
  • sleeps 2
  • 28 nights min
  • Air conditioning
  • Private garden

Price per night from

$143

Price per night from

$143

Distance approx 18.96 km from Summerland Key

14

Catchin' Moments Charters

Florida Keys / Key West

Key West yacht

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,083

Price per night from

$1,083

Distance approx 4.53 km from Summerland Key Show on Map

16

Conch Out

Lower Keys / Little Torch Key

Little Torch Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$140

Price per night from

$140

Distance approx 2.42 km from Summerland Key Show on Map

19

Lafitte Landing

Florida Keys / Cudjoe Key

Cudjoe Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$95

Price per night from

$95

Distance approx 2.48 km from Summerland Key Show on Map

13

Casa Rosa

Florida Keys / Ramrod Key

Ramrod Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$107

Price per night from

$107

Distance approx 4.8 km from Summerland Key Show on Map

10

Blue Heron

Florida Keys / Big Pine Key

Big Pine Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$86

Price per night from

$86

Distance approx 4.49 km from Summerland Key Show on Map

10

Mango House

Lower Keys / Little Torch Key

Little Torch Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$67

Price per night from

$67

Distance approx 2.23 km from Summerland Key Show on Map

19

Bahia Azul

Florida Keys / Ramrod Key

Ramrod Key house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$230

Price per night from

$230

Distance approx 7.51 km from Summerland Key

12

Green Turtle Landing

Florida Keys / Sugarloaf

Sugarloaf house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$140

Price per night from

$140

Distance approx 2.13 km from Summerland Key Show on Map

8

Quiet Waters

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$90

Price per night from

$90

Distance approx 2 km from Summerland Key Show on Map

28

Tropical Canal Home

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$192

Price per night from

$192

Distance approx 2.14 km from Summerland Key Show on Map

12

Coral House

Florida Keys / Ramrod Key

Ramrod Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$118

Price per night from

$118

Distance approx 5.49 km from Summerland Key

19

Bow Channel Manor

Florida Keys / Sugarloaf

Sugarloaf house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$188

Price per night from

$188