Some info has been automatically translated. Show original language

Summerland Key vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Summerland Key

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

Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 130 reviews

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 28 – Jan 4

G$158,337 GYD per night
Guest favorite

Home in Key West

4.94 out of 5 average rating, 268 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Aug 4 – 11

G$105,060 GYD per night
Guest favorite

Apartment in Key West

4.98 out of 5 average rating, 441 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Mar 16 – 23

G$71,068 GYD per night

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

Guest favorite

Condo in Key Colony Beach

4.92 out of 5 average rating, 191 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Feb 4 – 11

G$113,816 GYD per night
Guest favorite

Apartment in Key West

4.97 out of 5 average rating, 234 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Aug 20 – 27

G$74,165 GYD per night
Superhost

Home in Summerland Key

4.8 out of 5 average rating, 5 reviews

Bungalows at Sugarloaf Beach - Little Hammock

Feb 17 – 24

G$95,573 GYD per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Nov 20 – 27

G$24,710 GYD per night
Guest favorite

Home in Cudjoe Key

4.94 out of 5 average rating, 16 reviews

May Extravaganza - Relax in Paradise!

May 24 – 31

G$60,159 GYD per night
Guest favorite

Home in Summerland Key

4.95 out of 5 average rating, 21 reviews

Canal front cottage in Summerland Cove

Jun 12 – 19

G$102,636 GYD per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 38 reviews

Relaxing Home in the Keys

Aug 31 – Sep 7

G$43,005 GYD per night
Superhost

Home in Cudjoe Key

4.85 out of 5 average rating, 39 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Jun 4 – 11

G$136,594 GYD per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 45 reviews

Spanish Queen @Venture Out

Dec 11 – 18

G$80,167 GYD per night
Guest favorite

Camper/RV in Big Pine Key

4.91 out of 5 average rating, 34 reviews

Having fun in the lower Keys

Jul 6 – 13

G$34,476 GYD per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 24 reviews

Keys Island Villa - Venture Out Home 354

Sep 1 – 8

G$80,967 GYD per night
Guest favorite

Home in Cudjoe Key

5.0 out of 5 average rating, 18 reviews

Paradise in Cudjoe! Perfect Family Home!

Nov 15 – 22

G$80,717 GYD per night

Other great vacation rentals in Summerland Key

Guest favorite

Camper/RV in Big Pine Key

4.94 out of 5 average rating, 34 reviews

Delightful 1 bedroom camper with pool

Jul 9 – 16

G$36,950 GYD per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 37 reviews

Keys Cove

Aug 29 – Sep 5

G$81,831 GYD per night
Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 81 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

May 3 – 10

G$37,648 GYD per night
Superhost

Cottage in Cudjoe Key

4.94 out of 5 average rating, 52 reviews

Turtle Cove Views @ Venture Out - Waterfront

Jan 2 – 9

G$160,458 GYD per night
Guest favorite

Vacation home in Cudjoe Key

5.0 out of 5 average rating, 30 reviews

Beautiful Cottage & Amenities in Gated Community

Jun 21 – 28

G$66,723 GYD per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 5 reviews

Venture Out -Million Dollar Island Resort

Nov 23 – 30

G$65,648 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Nov 9 – 16

G$117,186 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun 8 – 15

G$32,044 GYD per night
Superhost

Home in Cudjoe Key

4.96 out of 5 average rating, 23 reviews

Cozy 2 br/2 bath home in Cudjoe

Oct 22 – 29

G$61,645 GYD per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

Aug 31 – Sep 7

G$143,568 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

Oct 12 – 19

G$163,295 GYD per night
Superhost

Home in Cudjoe Key

4.82 out of 5 average rating, 67 reviews

Tree Top Paradise

Nov 5 – 12

G$58,539 GYD per night

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

G$18,845 GYD before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Summerland Key?

    Yes! Work meets play with ease at over 80 vacation rentals in Summerland Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Summerland Key?

    Four-legged friends are welcome in Summerland Key. Choose from more than 90 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Summerland Key?

    Experience the best of Summerland Key with our cottage rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Summerland Key have self check-in?

    Absolutely! We offer over 30 house rentals with self check-in in Summerland Key. Enjoy a tailored experience with all the comforts you desire.

  • Are there Summerland Key cottage rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 cottage rentals with pools in Summerland Key, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Summerland Key have a bbq area?

    Absolutely! We offer over 60 house rentals with a bbq area in Summerland Key. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Summerland Key have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Summerland Key. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Summerland Key?

    Summerland Key has more than 150 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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