Cottage Rentals in Summerland Key, FL: Compare 10+ Sites & Save

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46 Best Cottage Rentals in Summerland Key (Starting from $200)

 Starfish Cottage - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Starfish Cottage - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
0.8k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
9.8

Exceptional

60 reviews

$243
Average price / night
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Ocean Breeze House - Sleeps 8 - ESCAPE THE COLD; OUR POOL IS HEATED!
Ocean Breeze House - Sleeps 8 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
0.8k from Summerland Key center

AC, Arcade, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

2 Bedrooms8 Guests
9.4

Superb

31 reviews

$430
Average price / night
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PALM COTTAGE - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
PALM COTTAGE - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
1.1k from Summerland Key center

AC, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.8

Exceptional

53 reviews

$267
Average price / night
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FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
1.1k from Summerland Key center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Grill

1 Bedroom4 Guests
9.8

Exceptional

47 reviews

$242
Average price / night
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SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!
SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
1.2k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
9.6

Exceptional

38 reviews

$200
Average price / night
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Peaceful ocean front cottage.
Peaceful ocean front cottage.
Cottage
Summerland Key, FL, 33042, United States
1.6k from Summerland Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$411
Average price / night
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**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Cottage
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

217 reviews

$464
Average price / night
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**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Cottage
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.6

Exceptional

45 reviews

$541
Average price / night
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Sea Breeze Cottage - Venture Out Unit 066
Sea Breeze Cottage - Venture Out Unit 066
Cottage
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
8.0

Good

17 reviews

$317
Average price / night
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Beautiful Cottage & Amenities in Gated Community
Beautiful Cottage & Amenities in Gated Community
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$788
Average price / night
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Canal front with open water views in Venture Out - Lot 529
Canal front with open water views in Venture Out - Lot 529
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$376
Average price / night
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35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Cottage
CUDJOE KEY, FL, 33042, United States
2.6k from Summerland Key center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
9.8

Exceptional

132 reviews

$420
Average price / night
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OCEANIA... water front cottage retreat ~
OCEANIA... water front cottage retreat ~
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$938
Average price / night
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Mile Marker Mahi - Venture Out #465
Mile Marker Mahi - Venture Out #465
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.6

Exceptional

55 reviews

$343
Average price / night
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FL Keys Cottage with Ocean Views - Venture Out Unit 395
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
8.4

Very Good

8 reviews

$317
Average price / night
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Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Balcony, Barbecue, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
9.6

Exceptional

14 reviews

$362
Average price / night
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Cozy, Perfect Conch Cottage! - VO315
Cozy, Perfect Conch Cottage! - VO315
Cottage
Summerland Key, FL, 33042, United States
2.7k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.2

Superb

33 reviews

$268
Average price / night
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2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cottage
Cudjoe Key, FL, 33042, United States
2.7k from Summerland Key center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
9.8

Exceptional

28 reviews

$648
Average price / night
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Breezy Point - Venture Out Unit 199
Breezy Point - Venture Out Unit 199
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$294
Average price / night
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Waterfront Home
Waterfront Home
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
8.8

Fabulous

179 reviews

$311
Average price / night
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A slice of paradise
A slice of paradise
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.0

Fabulous

98 reviews

$270
Average price / night
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Fishermen’s Paradise
Fishermen’s Paradise
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.2

Superb

99 reviews

$287
Average price / night
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waterfront cottage near key west, sleeps 6
waterfront cottage near key west, sleeps 6
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Arcade, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
9.4

Superb

28 reviews

$307
Average price / night
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NAUTILUS...ocean front cottage retreat ~
NAUTILUS...ocean front cottage retreat ~
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
8.8

Fabulous

6 reviews

$600
Average price / night
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Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
10.0

Exceptional

37 reviews

$255
Average price / night
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Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Cottage
Cudjoe Key, FL, 33042, United States
2.9k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

24 reviews

$215
Average price / night
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Canal front, dockage, 2 bedroom,  2 bath
Canal front, dockage, 2 bedroom, 2 bath
Cottage
Cudjoe Key, FL, 33042, United States
2.9k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
8.8

Fabulous

96 reviews

$351
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Cottage Rentals in Summerland Key.

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Frequently Asked Questions

You can explore 46 verified cottage rentals in Summerland Key. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Summerland Key vary based on the season, location, and amenities offered. Rates typically start from around $200 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Summerland Key feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 23 listings in Summerland Key welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Summerland Key are known for their comfort and charm, often including amenities such as Kitchen, Laundry, and Bedding/Linens. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Summerland Key are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.