Lower Sugarloaf Key vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Lower Sugarloaf 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!

Feb 25 – Mar 4

$759 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

$438 per night
Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 140 reviews

Casa Mariposa: Sombrero Beach Neighborhood

Book your getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, selected as 1 0f 24 amazing AirBNB rentals in the Keys, and 1 of 23 Amazing Airbnbs in The Keys. Step out the door from your private suite to a coral path that leads to our 50' heated/cooled lap pool, waterfall and large patio. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in an other lengths of stay.

May 3 – 10

$169 per night

Popular amenities for Lower Sugarloaf Key vacation rentals

Lower Sugarloaf Key house rentals

Guest favorite

Home in Marathon

4.96 out of 5 average rating, 118 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Sep 16 – 23

$345 per night
Guest favorite

Home in Marathon

4.9 out of 5 average rating, 155 reviews

Beachfront Villa - Florida Keys

Oct 5 – 12

$350 per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 115 reviews

Marathon one-level home on the Marina - with slip!

May 8 – 15

$517 per night
Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 162 reviews

Flakey's

Aug 17 – 24

$228 per night
Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 122 reviews

Ocean View 2/2 on Canal

Jun 25 – Jul 2

$359 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

$396 per night
Guest favorite

Home in Cudjoe Key

4.91 out of 5 average rating, 23 reviews

Relaxing and Inviting home with 35' dock

Jun 4 – 11

$197 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

$250 per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 38 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Jul 29 – Aug 5

$650 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

$269 per night
Guest favorite

Home in Cudjoe Key

4.94 out of 5 average rating, 18 reviews

Conch Cabana in Paradise 23 miles outside Key West

Aug 27 – Sep 3

$264 per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 45 reviews

Spanish Queen @Venture Out

Aug 23 – 30

$332 per night

Other great vacation rentals in Lower Sugarloaf Key

Superhost

Houseboat in Key West

4.9 out of 5 average rating, 189 reviews

Key West Luxury Houseboat

Aug 30 – Sep 6

$585 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

Jan 20 – 27

$295 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

$102 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

$156 per night
Guest favorite

Condo in Key West

4.99 out of 5 average rating, 83 reviews

Hidden Beach Duplex, Best Place in Key West

Aug 2 – 9

$608 per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

Sep 28 – Oct 5

$594 per night
Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 75 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Feb 24 – Mar 3

$728 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 31 – Aug 7

$142 per night
Guest favorite

Condo in Key West

4.94 out of 5 average rating, 33 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Apr 2 – 9

$349 per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun 7 – 14

$128 per night
Guest favorite

Camper/RV in Big Pine Key

4.94 out of 5 average rating, 34 reviews

Delightful 1 bedroom camper with pool

Jul 8 – 15

$152 per night
Guest favorite

Vacation home in Cudjoe Key

5.0 out of 5 average rating, 30 reviews

Beautiful Cottage & Amenities in Gated Community

Aug 23 – 30

$301 per night

Destinations to explore